University of Basel

Department
of Chemistry

Research Group Baudoin

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Publications

2025

103. 3-[Difluoro(4-nitrophenyl)methyl]-1,4,2-dioxazol-5-one (“K-Diox”)
A. Geraci, K. Antien, O. Baudoin Encyclopedia of Reagents for Organic Synthesis (EROS), 2025

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102. A C–H Arylation-Based Enantioselective Synthesis of Planar Chiral Cyclophanes
S. Huh, E. Linne, L. Estaque, G. Pieters, M. Devereux, O. Baudoin. Angew. Chem. Int. Ed.  2025, e202500653

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2024

101. Fe-Catalyzed α-C(sp3)–H Amination of N-Heterocycles
A. Geraci, O. Baudoin. Angew. Chem. Int. Ed. 2024, e202417414
Highlighted on Chemistry Views
Highlighted in the Organic Synthesis, Vol. 1, Issue 30

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100. 1,4-Pd Migration-Enabled Synthesis of Fused 4‑Membered Rings
M. Tsitopoulou, A. Clemenceau, P. Thesmar, O. Baudoin. J. Am. Chem. Soc. 2024, 146, 18811-18816
Highlighted in OPRD - Org. Process Res. Dev. 2025, 29(3), 603-615
Highlighted in Synfacts 2025, 21, 232
Highlighted by Douglass F. Taber on the Organic Chemistry Portal

 

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99. Total Synthesis of the Diterpenes (+)-Randainin D and (+)-Barekoxide via Photoredox-Catalyzed Deoxygenative Allylation
O. Vyhivskyi, O. Baudoin. J. Am. Chem. Soc. 2024, 146, 11486-11492
Highlighted on the University of Basel News
Highlighted in the Organic Synthesis, Vol. 1, Issue 5
Highlighted in Synfacts 2024, 20, 675.
Highlighted by Douglass F. Taber on the Organic Chemistry Portal

 

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98. Studies towards the Enantioselective Synthesis of Cryptowolinol via Pd0-Catalyzed C(sp3)–H Arylation/Parallel Kinetic Resolution
T. Miyakoshi, D. Kronenberg, S. Tamaki, R. Lombardi, O. Baudoin. Org. Lett. 2024, 26, 2923-2927

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97. Methylene C(sp3)−H Arylation Enables the Stereoselective Synthesis and Structure Revision of Indidene Natural Products
A. Kudashev, S. Vergura, M. Zuccarello, T. Bürgi, O. Baudoin, Angew. Chem. Int. Ed. 2024, 63, e2023161
 

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2023

96. Effect of α-Substitution on the Reactivity of C(sp3)–H Bonds in Pd0-Catalyzed C–H Arylation
M. Wheatley, M. Zuccarello, M. Tsitopoulou, S. A. Macgregor, O. Baudoin, ACS Catal. 2023,13,12563 -12570

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95. Iridium(III)-Catalyzed Intermolecular C(sp3)–H Amidation for the Synthesis of Chiral 1,2-Diamines
A. Geraci, U. Stojiljković, K. Antien, N. Salameh, O. Baudoin, Angew. Chem. Int. Ed.  2023, e202309263.

 

 

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94. A general enantioselective C–H arylation using an immobilized recoverable palladium catalyst
N. Salameh, F. Valentini, O. Baudoin, L. Vaccaro, ChemSusChem  2023, e202300609.

 

 

93. Simple synthetic access to [Au(IBiox)Cl] complexes
E. A. Martynova, M. Zuccarello, D. Kronenberg, M. Beliš, A. Czapik, Z. Zhang, K. Van Hecke, M. Kwit, O. Baudoin, L. Cavallo and S. P. Nolan, Dalton Trans. 2023
 

 

92. A C–H activation-based enantioselective synthesis of lower carbo[n]helicenes
S. Guo, S. Huh, M. Coehlo, L. Shen, G. Pieters, O. Baudoin, Nat. Chem. 2023
Highlighted on the University of Basel News
Highlighted in Synfacts 2023, 19, 770.

 

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2022

91. Remote Construction of N-Heterocycles via 1,4-Palladium Shift-Mediated Double C–H Activation
T. Miyakoshi, N. E. Niggli, O. Baudoin, Angew. Chem. Int. Ed.  2022, 61, e2021161.
Highlighted in Synfacts 2022, 632.

 

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90. C(sp3)–H Arylation Promoted by a Heterogeneous Palladium-N-Heterocyclic Carbene Complex in Batch and Continuous Flow
F. Francesco, I. Anastasiou, N. Salameh, T. Miyakoshi, O. Baudoin, L. Vaccaro, ChemSusChem  2022, 15, e2021027.

 

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2021

89. A Personal Account on Industrial Collaborations in the Field of C–H Activation
O. Baudoin, Chimia  2021, 75, 967–971.

 

88. Site-Selective Pd-Catalyzed C(sp3)−H Arylation of Heteroaromatic Ketones
A. Kudashev, O. Baudoin, Chem. Eur. J. 2021, 27, 17688-17694.

 

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87. A New Dioxazolone for the Synthesis of 1,2-Aminoalcohols via Iridium(III)-Catalyzed C(sp3)–H Amidation
K. Antien, A. Geraci, M. Parmentier, O. Baudoin, Angew. Chem. Int. Ed. 2021, 60, 22948-22955.
Highlighted in Synfacts2022, 17, 1243.

 

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86. Design of Chiral NHC‐Carboxylates as Potential Ligands for Pd‐Catalyzed Enantioselective C–H Activation
N. Niggli, O. Baudoin, Helv. Chim. Acta 2021, doi.org/10.1002/hlca.202100015.

 

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85. Pd0‐catalyzed Enantioselective Intramolecular Arylation of Enantiotopic Secondary C–H Bonds
R. Melot, M. Zuccarello, D. Cavalli, N. Niggli, M. Devereux, T. Bürgi, O. Baudoin, Angew. Chem. Int. Ed. 2021, 60, 7245-7250.

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84. Enantioselective Pd0‐Catalyzed C(sp2)–H Arylation for the Synthesis of Chiral Warped Molecules
D. Savary, O. Baudoin, Angew. Chem. Int. Ed. 2021, 60, 5136-5140.

 

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83. Chiral Catalysts for Pd0‐Catalyzed Enantioselective C–H Activation
O. Vyhivskyi, A. Kudashev, T. Miyakoshi, O. Baudoin, Chem. Eur. J. 2021, 27, 1231-1257.

 

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2020

82. Divergent Synthesis of Bioactive Dithiodiketopiperazine Natural Products Based on a Double C(sp3)–H Activation Strategy
P. Thesmar, S. Coomar, A. Prescimone, D. Häussinger, D. Gillingham, O. Baudoin, Chem. Eur. J. 2020, 26, 15298-15312.

 

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81. One-Pot Alkene Hydroboration/Palladium-Catalyzed Migratory Suzuki-Miyaura Cross-Coupling
Y. Baumgartner, O. Baudoin, ACS Catal. 2020, 10, 10508-10515.

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80. Direct Synthesis of Cyclopropanes from gem-Dialkyl Groups through Double C–H Activation
A. Clemenceau, P. Thesmar, M. Gicquel, A. Le Flohic, O. Baudoin, J. Am. Chem. Soc. 2020, 142, 15355-15361.
Highlighted by Jake Yeston in Science.
Highlighted in Synfacts 2020, 1308.
Highlighted on Chem-Station.com.
Highlighted by Douglass F. Taber on the Organic Chemistry Portal.
Abstract on the Organic Chemistry Portal.

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79. Synthesis of Amides and Esters by Pd0-Catalyzed Carbonylative C(sp3)-H Activation
T. Čarný, R. Rocaboy, A. Clemenceau, O. Baudoin, Angew. Chem. Int. Ed. 2020, 59, 18980-18984.
Highlighted in Synfacts 2020, 1193.

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78. Multiple Catalytic C–H Bond Functionalization for Natural Product Synthesis
O. Baudoin, Angew. Chem. Int. Ed. 2020, 59, 17798-17809.

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77. Intermolecular Palladium(0)-Catalyzed Atropo-enantioselective C−H Arylation of Heteroarenes
Q.-H. Nguyen, S.-M. Guo, T. Royal, O. Baudoin, N. Cramer, J. Am. Chem. Soc. 2020, 142, 2161-2167

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2019

76. Efficient and Divergent Total Synthesis of (−)-Epicoccin G and (−)-Rostratin A Enabled by Double C(sp3)–H Activation
P. Thesmar, O. Baudoin, J. Am. Chem. Soc.2019, 141, 15779-15783.
Highlighted in Synfacts 2019, 1341 and Synfacts 2019, 1423.

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75. Regiodivergent enantioselective C–H functionalization of Boc-1,3-oxazinanes for the synthesis of β2- and β3-amino acids
W. Lin, K.-F. Zhang, O. Baudoin, Nature Catalysis 2019, 2, 882-888
Highlighted by Douglass F. Taber on the Organic Chemistry Portal

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74. Redox‐Neutral Coupling between Two C(sp3)–H Bonds Enabled by 1,4‐Palladium Shift for the Synthesis of Fused Heterocycles
R. Rocaboy, I. Anastasiou, O. Baudoin, Angew. Chem. Int. Ed. 2019, 58, 14625-14628.

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73. Total Synthesis of (Nor)illudalane Sesquiterpenes Based on a C(sp3)–H Activation Strategy
R. Melot, M. V. Craveiro, O. Baudoin,  J. Org. Chem.2019, 84, 12933-12945.
Highlighted by Douglass F. Taber on the Organic Chemistry Portal

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72. 1,4-Palladium Shift/C(sp3)-H Activation Strategy for the Remote Construction of Five-Membered Rings
R. Rocaboy, O. Baudoin, Org. Lett. 2019, 21, 1434-1437

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71. Divergent Enantioselective Synthesis of (Nor)illudalane Sesquiterpenes via Pd0‑Catalyzed Asymmetric C(sp3)−H Activation
R. Melot, M. V. Craveiro, T. Bürgi, O. Baudoin, Org. Lett. 2019, 21, 812-815

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70. Pd-catalyzed γ-arylation of γ,δ-unsaturated O-carbamates via an unusual haptotropic rearrangement
T. Royal, O. Baudoin, Chem. Sci.2019, 10, 2331-2335

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2018

69. Domino Pd0‐Catalyzed C(sp3)‐H Arylation/Electrocyclic Reactions via Benzazetidine Intermediates
R. Rocaboy, D. Dailler, F. Zellweger, M. Neuburger, C. Salomé, E. Clot, O. Baudoin, Angew. Chem. Int. Ed. 2018, 57, 12131-12135

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68.  A Four-Step Synthesis of (±)-γ-Lycorane via Pd0-Catalyzed Double C(sp2)–H/C(sp3)–H Arylation
R. Rocaboy, D. Dailler, O. Baudoin, Org. Lett. 2018, 20, 772-775

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67. Barbier-Negishi Coupling of Secondary Alkyl Bromides with Triflates and
Nonaflates
K.-F. Zhang, F. Christoffel, O. Baudoin, Angew. Chem. Int. Ed., 2018, 57, 1982-1986

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66.  Chiral Bifunctional Phosphine-Carboxylate Ligands for Palladium(0)-Catalyzed Enantioselective C−H Arylation
L. Yang, M. Neuburger, O. Baudoin, Angew. Chem. Int. Ed., 2018, 57, 1394-1398

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2017

65. Synthesis of β-Lactams by Palladium(0)-Catalyzed C(sp3)−H Carbamoylation
D. Dailler, R. Rocaboy, O. Baudoin, Angew. Chem. Int. Ed., 2017, 56, 7218-7222
Highlighted by Douglass F. Taber on the Organic Chemistry Portal

A chemical reaction scheme shows a starting material with R1, R2, R3 groups reacting with Pd0/L cat., CO (3 equiv), PivOH cat., Cs2CO3, 120 °C to form a product with R1, R2, R3 groups. Several other products are shown, including one with NH3Cl and CO2H groups. A list of four bullet points reads: redox neutral, stoichiometric CO (COgen), 1ary, 2ary, activated 3ary C-H bonds, enantioselective.

64. Ferrocene derivatives of liquid chiral molecules allow assignment of absolute configuration by X-ray crystallography
P. M. Holstein, J. J. Holstein, E. C. Escudero-Adán, O. Baudoin, A. M. Echavarren, Tetrahedron Asymmetry, 2017, 28, 1321-1329

Three images in a row show a chemical process. First, a vial with a yellow liquid and a chemical formula. Second, a brown crystal. Third, a crystal structure diagram. Arrows and a chemical formula are between the images.

63. Ring Construction by Palladium(0)-Catalyzed C(sp3)−H Activation
O. Baudoin, Acc. Chem. Res. 2017, 50, 1114-1123

A chemical reaction scheme shows a substrate reacting with a Pd0/L catalyst and a base to form a fused 4- to 7-membered ring. Below, five examples of complex organic molecules are shown, including "aeruginosin 298A" and "Indaziflam".

62. Palladium(0)-catalyzed asymmetric C(sp3)–H arylation using a chiral Binol-derived phosphate and an achiral ligand
L. Yang, R. Melot, M. Neuburger, O. Baudoin, Chem. Sci.2017, 8, 1344-1349

A chemical reaction scheme shows a reactant with a benzene ring and an X group, reacting to form a product with a five-membered ring. Reagents include Pd(PCy3)2 (5 mol%), BPA (10 mol%), Cs2CO3 (3 equiv), DME, 4Å MS, 120 °C. The product has 27 examples, e.r. up to 98:2. The structure of BPA is shown, with Ar = (3,5-di-CF3)Ph.

61. Enantioselective α-Arylation of O-Carbamates via Sparteine-Mediated Lithiation and Negishi Cross-Coupling
T. Royal, Y. Baumgartner, O. Baudoin, Org. Lett. 2017, 19, 166-169
Highlighted by Douglass F. Taber on the Organic Chemistry Portal

A chemical reaction scheme shows a starting molecule with R1, H, H, O, C, O, NR2. An arrow points to the right, with s-BuLi/(-)-sp, then Zn(OAc)2, then Pd0/L cat., ArX above it. The product is a molecule with Ar, R1, O, C, O, NR2, with "er up to 99.5:0.5" below it. Two arrows point down from this product. The left arrow has H-B(pin) above it, leading to a molecule with Ar, H, R1, O, H, and "2ary alcohol" below it. The right arrow has R3-B(pin) above it, leading to a molecule with Ar, R3, R1, O, H, and "3ary alcohol" below it.

60. Comparative Structural Analysis of Biarylphosphine Ligands in Arylpalladium Bromide and Malonate Complexes
A.-S. Goutierre, H. V. Trinh, P. Larini, R. Jazzar, O. Baudoin, Organometallics, 2017, 36, 129-135

A chemical reaction scheme shows a μ-bridged dimer or monomer reacting with MeO-C(OK)=CH-C(O)OMe to form a κ² malonate complex. The structure of L is also shown. Ar = Ph, imid; R¹ = NMe₂, i-Pr; R² = H, NMe₂.

2016

59. Terminal-selective functionalization of alkyl chains by regioconvergent cross-coupling
S. Dupuy, K.-F. Zhang, A.-S. Goutierre, O. Baudoin, Angew. Chem. Int. Ed., 2016, 55, 14793-14797

Chemical reaction scheme showing R1-CH(Br)-(CH2)n + R2-OTf reacting under Pd0/L cat., Mg, LiCl, ZnCl2, Barbier conditions to form R1-(CH2)n+1-R2, the major linear product. The first reactant is described as "isolated or mixtures of 2ary alkyl bromides".

58. Selectivity Control in the Palladium catalyzed Cross-coupling of Alkyl Nucleophiles
O. Baudoin, CHIMIA2016, 70, 768-772

57. Applications of catalytic organometallic C(sp3)–H Bond functionalization
D. Dailler, G. Danoun, O. Baudoin, in Top. Organomet. Chem. (Eds. : P. H. Dixneuf, H. Doucet), Vol. “C–H bond activation and catalytic functionalization II”, 2016, 133-154

56. Synthesis of Conformationally Constrained Esters and Amines by Pd-Catalyzed α-Arylation of Hindered Substrates
A. Martin, Jean-Pierre Vors, O. Baudoin, ACS Catal. 2016, 6, 3941-3945

A chemical reaction scheme showing the synthesis of conformationally constrained benzyl- and phenethylamines. The reaction starts with two bulky reactants, leading to a very bulky intermediate, which then forms two final products.

55. Synthesis of Strained γ-Lactams by Palladium(0)-Catalyzed C(sp(3) )-H Alkenylation and Application to Alkaloid Synthesis
P. M. Holstein, D. Dailler, J. Vantourout, J. Shaya, A. Millet, O. Baudoin,* Angew. Chem. Int. Ed.2016, 55, 2805-2809
Highlighted by Douglass F. Taber on the Organic Chemistry Portal

A chemical reaction scheme shows a six-membered ring with a nitrogen atom and an oxygen atom, reacting with Pd0/PPh3 cat. and CsOPiv to form a five-membered ring. This then reacts to form mono- and bicyclic alkaloids.

54. Electrophilic trifluoromethylation of carbonyl compounds and their nitrogen analogues under copper catalysis
A.Prieto, O. Baudoin, N.Monteiro, D.Bouyssi, Chem. Commun. 2016, 52, 869-881

A chemical reaction diagram shows a central box with "Cu + Electrophilic CF3". Green arrows point from the box to eight surrounding chemical structures.

2015

53.  C–C bond formation by Alkyl C–H activation
O.Baudoin, in Science of Synthesis, catalytic transformations via C–H activation 2 (Ed. : J.Q. Yu), Georg Thieme Verlag KG,2015, Chapter 2.2,37-62

A chemical reaction diagram shows a molecule with a central carbon atom bonded to three other atoms and a hydrogen atom, reacting to form a molecule with a central carbon atom bonded to three other atoms and a carbon atom. The reaction arrow is labeled "MLn cat." above and "reagents" below.

52. Copper-catalyzed trifluoromethylation of aliphatic N-arylhydrazones : A concise synthetic entry to 2-trifluoromethylindoles from simple aldehydes
A.Prieto, M. Landart, O. Baudoin, N.Monteiro, D.Bouyssi, Adv.Synth.Catal. 2015, 357, 2939-2943

Chemical reaction scheme showing the synthesis of trifluoromethylated hydrazones from aliphatic aldehydes, followed by Fischer indole synthesis. The first step shows 17 examples with up to 97% yield, and the second step shows 5 examples with up to 96% yield.

51. Divergent synthesis of aeruginosins based on a C(sp3)–H activation strategy
D. Dailler, G. Danoun, B. Ourri, O. Baudoin, Chem. Eur. J.  2015, 21, 9370-9379.
Highlighted by Douglass F. Taber on the Organic Chemistry Portal

A chemical diagram shows two molecules, one above the other. The top molecule has a blue line and the text "C(sp³)−H alkenylation". The bottom molecule has a red line and the text "C(sp³)−H arylation". Below both molecules is the text "aeruginosins".

50. Efficient Pd0-catalyzed asymmetric activation of primary and secondary C–H bonds enabled by modular binepine ligands and carbonate bases
P. M. Holstein, M. Vogler, P. Larini, G. Pilet, E. Clot, O. Baudoin, ACS Catal. 2015, 5, 4300-4308

A chemical reaction scheme shows a reactant molecule with a Br and H atom, reacting under conditions of Pd2dba3/L* cat., CO32-, DMSO, ≥90 °C, to form a product molecule with 2-3 adjacent stereocenters, high d.r., e.r. up to 98:2. The structure of L* is also shown.

49. Palladium-catalyzed β-selective C(sp3)–H arylation of N-Boc-piperidines
A. Millet, O. Baudoin, Org. Synth. 2015, 92, 76-90

48. A general and scalable synthesis of aeruginosin marine natural products based on two strategic C(sp3)–H activation reactions
D. Dailler, G. Danoun, O. Baudoin, Angew. Chem. Int. Ed.2015, 54, 4919-4922
Highlighted by Douglass F. Taber on the Organic Chemistry Portal

A chemical structure diagram shows a molecule with the label "aeruginosins". Two reactions are indicated with arrows: "intramolecular C(sp³)-H alkenylation" and "intermolecular C(sp³)-H arylation".

2014

47. Mechanistic study on the selectivity of olefin vs. cyclobutene formation by palladium(0)-catalyzed intramolecular C(sp3)–H activation
C. E. Kefalidis, M. Davi, P. M. Holstein, E. Clot, O. Baudoin, J. Org. Chem.2014, 79, 11903-11910

A chemical reaction diagram shows a starting molecule, a 2-bromophenylacetonitrile derivative, reacting with Pd0/P(t-Bu)3 cat. and K2CO3 to form two products: a phenylacetonitrile derivative with an alkene group and a cyclobutane derivative. An intermediate 5-membered palladacycle is also shown.

46. Copper-catalyzed β-trifluoromethylation of conjugated hydrazones
A. Prieto, E. Jeamet, N. Monteiro, D. Bouyssi, O. Baudoin, Org. Lett. 2014, 16, 4770-4773

A chemical reaction scheme shows a starting molecule with R1 and R2 groups, reacting with F3C-I-O-C6H4-C=O (1.2 equiv) in the presence of CuCl (10 mol %) and CHCl3 at 20 °C. This yields two possible products: one with a CF3 group attached to the carbon with R1, and another (when R2 = H) with a CF3 group attached to the carbon adjacent to the R1 group. The reaction has 19 examples, up to 87% yield.

45. Efficient Pd-catalysed allene synthesis from alkynes and aryl bromides via an intramolecular base assisted deprotonation (iBAD) mechanism
N. Nella, E. Parker, J. Hitce, P. Larini, R. Jazzar, O. Baudoin, Chem. Eur. J. 2014, 20, 13272-13278

Chemical reaction scheme showing a benzene ring with Br and R1, reacting with an alkyne with R2 and R3, in the presence of [Pd2(dba)3] / DFOTP, Cs2CO3, PivOH, to form a benzene ring with R1 and an allene with R2 and R3. To the right, a mechanism called "intramolecular Base-Assisted Deprotonation mechanism 'iBAD'" is shown.

44. Palladium-catalyzed γ-selective arylation of zincated Boc-allylamines
A. Millet, O. Baudoin, Org. Lett. 2014, 16, 3998-4000
Highlighted in Synfacts 2014, 1190

Chemical reaction scheme showing a starting molecule with R, N, and Boc groups, and an allyl chain. Reagents n-BuLi, TMEDA, THF, then ZnCl2, then Pd2dba3/SPhos cat., Ar-Br, toluene, 60 °C lead to a product molecule with R, N, and Boc groups, and an E-configured double bond, followed by a gamma-carbon and an Ar group.

43. Synthesis of 1-indanols and 1-indanamines by intramolecular palladium(0)-catalyzed C(sp3)–H arylation: impact of conformational effects
S. Janody, R. Jazzar, A. Comte, P. M. Holstein, J.-P. Vors, M. J. Ford, O. Baudoin, Chem. Eur. J. 2014, 20, 11084-11090

A chemical reaction scheme shows a substituted benzene ring with a bromine atom and an alkyl chain with R1, R2, Y, and H groups. An arrow points to a product where the bromine and H atoms are replaced by a new ring closure. Reagents are Pd(PPh3)4 cat., K2CO3/PivOK, xylenes, 140 degrees Celsius. Text below the structures states "Y = OR, NR2", "R1, R2 affect efficiency", and "Y affects diastereoselectivity".

42. Ligand-controlled arylation of acyclic N-Boc-amines
A. Millet, D. Dailler, P. Larini, O. Baudoin, Angew. Chem. Int. Ed. 2014, 53, 2678-2682
Highlighted in Synfacts 2014, 524

A chemical reaction scheme shows a starting molecule R-N(Boc)-CH(alpha)-CH(beta) with hydrogens on alpha and beta carbons. An arrow points to two possible products: R-N(Boc)-CH(alpha)-Ar or R-N(Boc)-CH2-CH(beta)-Ar. Reagents are s-BuLi, then ZnCl2, then Ar-X, Pd0/L cat. L is P(t-Bu)3 or a phenyl-substituted imidazole with P(i-Bu)2.

41. C-H Bond Alkylation (Including Hydroarylation of Alkenes)
L. Jean-Gérard, R. Jazzar, O. Baudoin, in Metal Catalyzed Cross-Coupling Reactions and More (Eds.: A. De Meijere, S. Bräse, M. Oestreich), Wiley-VCH, Weinheim, 2014, Vol. 3, chapter 19, 1427-1493

2013

40. Palladium-catalyzed β-arylation of silyl ketene acetals and application to the synthesis of benzo-fused δ-lactones
S. Aspin, L. López-Suárez, P. Larini, A.-S.Goutierre, R. Jazzar, O. Baudoin, Org. Lett.2013, 15, 5056-5059

A chemical reaction scheme shows a starting material reacting with Ar-Br in the presence of Pd/L cat., ZnF2, DMF, and 80-120 °C to form an intermediate. This intermediate then forms two products: dihydrocoumarins and 1-isochromanones.

39. Copper-catalyzed trifluoromethylation of N,N-dialkylhydrazones
E. Pair, N. Monteiro, D. Bouyssi, O. Baudoin, Angew. Chem. Int. Ed. 2013, 52, 5346-5349

A chemical reaction scheme shows a starting material, a reagent, and a product. The starting material is R-C(H)=N-N(Alk)2. The reagent is a benzene ring with an iodine atom and a CF3 group attached, and a carboxylate group. The reaction conditions are CuCl (cat.), CHCl3, 20°C. The product is R-C(CF3)=N-N(Alk)2.

38. Ligand-controlled β-selective C(sp3)–H arylation of N-Boc-piperidines
A. Millet, P. Larini, E. Clot, O. Baudoin, Chem. Sci. 2013, 4, 2241-2247

A chemical reaction scheme shows a piperidine derivative reacting with s-BuLi, TMEDA, then ZnCl2, then Ar-X, Pd0/L cat. to form an aryl-substituted piperidine derivative. The catalyst L is 1-phenyl-2-(diisopropylphosphino)pyrrole.

37. Intramolecular PdII-catalyzed dehydrogenative C(sp3)–C(sp2) coupling: an alternative to Pd0-catalyzed C(sp3)–H arylation from aryl halides?
C. Pierre, O. Baudoin, Tetrahedron (Symposium-in-Print on Metal-Catalyzed C–H Functionalization)2013, 69, 4473-4478

A chemical reaction scheme shows a starting molecule with a five-membered ring containing X and Y, and an attached chain with an i-Pr group and a CN group. An arrow points to a product molecule, a fused ring system with a new five-membered ring. Reagents are Pd(OAc)2 cat., Ag2CO3, PivOH. Below the product, X = S, Y = CH, N.

2012

36. Synthesis of aromatic α-amino esters:  Pd-catalyzed long-range arylation of primary C(sp3)–H bonds
S. Aspin, A.-S. Goutierre, P. Larini, R. Jazzar, O. Baudoin, Angew. Chem. Int. Ed.2012, 51, 10808-10811
Highlighted in Synfacts 2013, 81
Highlighted by Douglass F. Taber on the Organic Chemistry Portal

A chemical reaction scheme shows a starting molecule with formula H-(CH2)n-CH(NBn2)-CO2Me reacting under conditions a) R2NLi, Pd0/L cat., Ar-Br and b) hydrogenolysis to form Ar-(CH2)n-CH(NH2)-CO2Me. The reaction is described as β-ζ arylation, with n = 0-4, and 27 examples.

35. Synthesis of hexahydroindoles by intramolecular C(sp3)–H alkenylation - Application to the synthesis of the core of aeruginosins
J. Sofack-Kreutzer, N. Martin, A. Renaudat, R. Jazzar, O. Baudoin, Angew. Chem. Int. Ed.2012, 51, 10399-10402
Highlighted by Douglass F. Taber on the Organic Chemistry Portal

A chemical reaction scheme shows a bicyclic compound with a bromine atom and R groups reacting with Pd0/L cat. and base to form a tricyclic compound. This is followed by a double arrow pointing to a similar tricyclic compound with a COCF3 group and an OH group, labelled "octahydroindole core of aeruginosins".

34. Synthesis of cyclobutarenes by palladium-catalyzed C(sp3)–H bond arylation: preparation of methyl 7-methylbicyclo[4.2.0]octa-1,3,5-triene-7-carboxylate
M. Davi, A. Comte, R. Jazzar, O. Baudoin, Org. Synth.2012, 89, 510-518

33. Diastereo- and enantioselective intramolecular C(sp3)–H arylation for the synthesis of fused cyclopentanes
N. Martin, C. Pierre, M. Davi, R. Jazzar, O. Baudoin, Chem. Eur. J.2012, 18, 4480-4484
Highlighted in Synfacts 2012, 755

A chemical reaction scheme shows a reactant molecule with a benzene ring and a side chain, reacting with Pd(OAc)2/L*, K2CO3, and DMSO at 140 °C to form a product molecule. The product has a fused ring system. Below the product, the yield is 72% to 95%, d.r. is 12:1 to 31:1, and e.r. is 76:24 to 90:10. To the right, the structure of L* is shown.

32. On the mechanism of the palladium-catalyzed β-arylation of ester enolates
P. Larini, C. E. Kefalidis, R. Jazzar, A. Renaudat, E. Clot, O. Baudoin Chem. Eur. J.2012, 18, 1932-1944

A chemical reaction scheme shows Ar-Br and a lithium enolate reacting to form an alpha-arylation product and a beta-arylation product. The reaction proceeds via a Pd enolate, which isomerizes to a Pd homoenolate in the rate-determining step. Both intermediates undergo reductive elimination to yield the products.

31. Synthesis of tricyclic nitrogen heterocycles by a sequence of palladium-catalyzed N–H and C(sp3)–H arylations
M. Guyonnet, O. Baudoin, Org. Lett.2012, 14, 398-401

Chemical reaction scheme showing a C(sp3)-H arylation followed by N-arylation/bromination. The first step transforms a cyclic compound into an N-arylated and brominated product. The second step shows the cleavage into two separate molecules.

2011

30. Transition metal-catalyzed arylation of unactivated C(sp3)–H bonds
O. Baudoin, Chem. Soc. Rev.2011, 40, 4902-4911 (review, special issue on "Cross coupling reactions in organic synthesis")

A chemical reaction diagram shows a carbon atom bonded to three other atoms and a hydrogen atom. A green arrow labeled "[M]" points to the bond between carbon and hydrogen. An arrow labeled "Ar-X" points to the right, showing the product where the hydrogen atom is replaced by an "Ar" group.

29. Synthesis of polycyclic molecules by double C(sp2)–H/C(sp3)–H arylations with a single palladium catalyst
C. Pierre, O. Baudoin, Org. Lett. 2011, 13, 1816-1819

Chemical reaction scheme showing two different starting materials reacting with Ar-X under Pd0/PR3 catalyst and base to form two different products. The first product is formed in 11 examples with 37-82% yield. The second product is formed in 5 examples with 60-87% yield.

2010

28. DFT study of the mechanism of benzocyclobutene formation by palladium-catalysed C(sp3)–H activation: role of the nature of the base and the phosphine
C. E. Kefalidis, O. Baudoin, E. Clot, Dalton Trans.2010, 39, 10528-10535 (special issue on "Catalytic C-H and C-X bond activation")

Two molecular diagrams are shown side by side. The left diagram is labelled "PtBu3 / CO32-" and the right diagram is labelled "PMe3 / AcO-". The title of the image is "C-H Activation Lowest TS".

27. The palladium-catalyzed β-arylation of carboxylic esters
A. Renaudat, L. Jean-Gérard, R. Jazzar, C. E. Kefalidis, E. Clot, O. Baudoin, Angew. Chem. Int. Ed.2010, 49, 7261-7265
VIP - Highlighted in Synfacts 2010, 1409

A chemical reaction scheme shows an aryl halide reacting with an alpha-substituted ester to form an alpha-aryl ester. The reaction is catalyzed by Pd/L and Cy2NLi in toluene at 22–110 °C.

26. Intramolecular palladium-catalyzed alkane C–H arylation from aryl chlorides
S. Rousseaux, M. Davi, J. Sofack-Kreutzer, C. Pierre, C. E. Kefalidis, E. Clot, K. Fagnou, O. Baudoin, J. Am. Chem. Soc.2010, 132, 10706-10716

A chemical reaction scheme shows a starting molecule with an Ar group, a Z group, and R1, R2, Cl, and H atoms. An arrow points to the right, with "Pd0/PR3 cat.", "base, 140 °C" written above and below it. The product molecule has a cyclic structure with an Ar group, a Z group, and R1 and R2 atoms. Below the product are the words "42 examples" and "47-96% yield".

25. Synthesis of antimicrotubule dibenzoxepines
V. Colombel, A. Joncour, S. Thoret, J. Dubois, J. Bignon, J. Wdzieczak-Bakala, O. Baudoin, Tetrahedron Lett.2010, 51, 3127-3129

A chemical reaction scheme shows two reactants on the left, 2-bromo-4-R2-benzyl alcohol and 2-(hydroxymethyl)-3,4,5,6-tetramethoxybenzene-1-boronic acid pinacol ester, reacting to form a tricyclic product on the right.

24. Functionalization of organic molecules by transition-metal catalyzed C(sp3)–H activation
R. Jazzar, J. Hitce, A. Renaudat, J. Sofack-Kreutzer, O. Baudoin, Chem. Eur. J.2010, 16, 2654-2672 (review)

A chemical reaction diagram shows a carbon atom bonded to three other atoms and a hydrogen atom (C-H). A curved arrow indicates the addition of a metal catalyst [M], forming C-[M]. A second curved arrow shows the addition of X and the removal of [M], resulting in C-X.

2009

23. Synthetic approaches to amino analogues of N-acetylcolchinol
V. Colombel, O. Baudoin, J. Org. Chem. 2009, 74, 4329-4335

A chemical reaction scheme shows a three-step synthesis. The first step reacts a biphenyl aldehyde with RMgBr. The second step reacts the product with aqueous HF. The final product is a cyclic ether.

22. Cycloadditions of 1,1-disubstituted benzocyclobutenes obtained by C(sp3)–H activation
M. Chaumontet, P. Retailleau, O. Baudoin, J. Org. Chem.2009, 74, 1774-1776

A chemical reaction scheme showing a bicyclic compound with a benzene ring fused to a cyclobutane ring, reacting with a maleimide derivative under MW irradiation to form a tricyclic product. The product is described as a "single diastereoisomer", with "17 examples" and "61-96% yield".

21. Synthesis of 3,4-dihydroisoquinolines by a C(sp3)–H activation/electrocyclization strategy: total synthesis of coralydine
M. Chaumontet, R. Piccardi, O. Baudoin, Angew. Chem. Int. Ed.2009, 48, 179-182

A chemical reaction scheme shows three molecular structures connected by arrows. The first structure, labeled 1, is a substituted benzene ring. The second structure, labeled 2, is a substituted quinoline. The third structure is (±)-coralyne.

2008

20. Synthesis of benzocyclobutenes by palladium-catalyzed C–H activation of methyl groups: method and mechanistic study
M. Chaumontet, R. Piccardi, N. Audic, J. Hitce, J.-L. Peglion, E. Clot, O. Baudoin, J. Am. Chem. Soc. 2008, 130, 15157-15166.
Highlighted by Douglass F. Taber on the Organic Chemistry Portal.

A chemical reaction scheme shows a benzene derivative reacting to form a cyclobutane derivative. Reagents are Pd(OAc)2, P(t-Bu)3 cat., K2CO3, DMF, 140 °C. The product is achieved in up to 92% yield. A ball-and-stick model of a computed transition state is shown.

19. Synthesis of anti-microtubule biaryls and preliminary evaluation as vascular-disrupting agents
A. Joncour, J.-M. Liu, A. Décor, S. Thoret, J. Wdzieczak-Bakala, J. Bignon, O. Baudoin, ChemMedChem 2008, 3, 1731-1739

A chemical structure diagram shows a molecule with two benzene rings connected by a single bond. One ring has two methoxy groups and one OR2 group. The other ring has two methoxy groups and one OMe group.

18. Substituted benzocarbocycles by palladium-catalyzed cascade reactions featuring a C(sp3)−H activation step
J. Hitce, O. Baudoin, Adv. Synth. Catal.  2007, 349, 2054-2060

A chemical reaction scheme shows a starting molecule with a benzene ring, a chlorine atom, a bromine atom, and a carbon chain with a nitrile group. This reacts with Pd(0) and Base, undergoing C(sp3)-H activation and Heck cyclization, to form an intermediate molecule with a benzene ring fused to a four-membered ring, which has a double bond and a nitrile group. This intermediate then undergoes either Heck arylation with ArBr to form a product with an aryl group, or hydrogenation with H2 to form a product with two hydrogen atoms.

17. Synthesis of tubulin-binding bridged biaryls via intermolecular Suzuki coupling
O. Baudoin, C. R. Chimie  2008, 11, 38-42 (account)

2007

16. Asymmetric synthesis of antimicrotubule biaryl hybrids of allocolchicine and steganacin
A. Joncour, A. Décor, J.-M. Liu, M.-E. Tran Huu Dau, O. Baudoin, Chem. Eur. J. 2007, 13, 5450-5465

A chemical reaction scheme shows a three-step synthesis. The first step, Pd0 cat. and Ar-B(pin), converts a benzene derivative with an S-chiral alcohol to a biphenyl derivative with an aR-chiral axis and an S-chiral alcohol. The second step, - H2O, converts the biphenyl derivative to a cyclic biphenyl derivative with an aR-chiral axis and an R-chiral center. The enantiomeric excess (ee) is 96-98% for the starting material and 94-96% for the final product.

15. New approaches for the decarboxylative biaryl coupling
O. Baudoin, Angew. Chem. Int. Ed. 2007, 46, 1373-1375
Angew. Chem.  2007, 119, 1395-1397 (Highlight)

 

 

Chemical reaction diagram showing Ar1-CO2H plus Ar2-Br reacting to form Ar1-Ar2, with Pd0 cat. above the reaction arrow and -CO2 and -HBr below it.

14. A new synthetic approach to biaryls of the rhazinilam type. Application to synthesis of three novel phenylpyridine-carbamate analogues
A.-L. Bonneau, N. Robert, C. Hoarau, O. Baudoin, F. Marsais, Org. Biomol. Chem.2007, 5, 175-183

A chemical reaction scheme shows a three-step synthesis. The first step converts a phenyl-cyclobutane-methanol derivative to a dilithium intermediate. The second step reacts this intermediate with a bromopyridine derivative, followed by TBSCl and Chloranil, to form a substituted pyridine. The third step shows the conversion of this pyridine to a tricyclic product with a variable Y group.

13. Palladium-catalyzed intramolecular C(sp3)–H functionalization: catalyst development and synthetic applications
J. Hitce, P. Retailleau, O. Baudoin, Chem. Eur. J. 2007, 13, 792-799

A chemical reaction scheme shows a benzene ring with a bromine atom and a carbon atom with two Alk groups and a cyano group. An arrow points to the right, with Pd(OAc)2, a green benzene ring with a fluorine atom and a P(CH3)3 group, K2CO3, DMF, and 100 °C written above and below it. To the right are three product structures, two of which are cyclic.

2006

12. Biaryl Axis as a stereochemical relay for the asymmetric synthesis of antimicrotubule agents
A. Joncour, A. Décor, S. Thoret, A. Chiaroni, O. Baudoin, Angew. Chem. Int. Ed. 2006, 45, 4149-4152

A chemical reaction scheme shows a three-step synthesis. The first step, a Suzuki-Miyaura coupling, converts an aryl iodide to a biaryl alcohol. The second step, an acid-catalyzed cyclization, forms a cyclic ether. Enantiomeric excess values are given for the starting material (96-98% ee) and the final product (88-96% ee).

11. Synthesis and biological evaluation of B-ring analogues of (–)-rhazinilam
A. Décor, B. Monse, M.-T. Martin, A. Chiaroni, S. Thoret, D. Guénard, F. Guéritte, O. Baudoin, Bioorg. Med. Chem. 2006, 14, 2314-2332

Two chemical structures are shown. The first structure has rings labelled A, B, C, D, and an arrow pointing to a bond labelled "carbamate, amino-acid". The second structure has rings labelled A, B, C, D, and substituents R1 and R2.

10. In vitro oxidative metabolism study of (–)-rhazinilam
A. Décor, D. Bellocq, O. Thoison, N. Lekieffre, A. Chiaroni, J. Ouazzani, T. Cresteil, F. Guéritte, O. Baudoin, Bioorg. Med. Chem. 2006, 14, 1558-1564

A chemical reaction diagram shows the molecule (-)-rhazinilam, with two blue arrows pointing from the text "cytochrome P450 bio-oxidation" to positions 3 and 5 on the molecule.

2005

9.  The asymmetric Suzuki coupling route to axially chiral biaryls
O. Baudoin, Eur. J. Org. Chem.  2005, 4223-4229 (review)

A chemical reaction scheme shows a benzene ring with R1 and Hal substituents, plus a benzene ring with R3, R4, and B(OR)2 substituents, reacting to form a chiral biphenyl product. The reaction is catalyzed by Pd0 and a chiral reactant or ligand.

2004

8.  The chemistry and biology of rhazinilam and analogues
O. Baudoin, D. Guénard, F. Guéritte, Mini-Reviews in Organic Chemistry, 2004, 1, 333-341 (review)

2003

7.  The palladium-catalyzed C–H activation of benzylic gem-dialkyl groups
O. Baudoin, A. Herrbach, F. Guéritte, Angew. Chem. Int. Ed.  2003, 42, 5736-5740

A chemical reaction scheme shows a starting molecule with a benzene ring and a bromine atom, reacting with Pd(OAc)2, P(o-tol)3 cat., K2CO3, and DMF at 150 degrees Celsius. This yields two possible products: one with a benzene ring and a vinyl group (R1 = Me), and another with a fused four-membered ring (R1 = H).

6. A novel 1,3-central-to-axial chirality induction approach to cyclooctadiene lignans
O. Baudoin, A. Décor, M. Cesario, F. Guéritte, Synlett 2003, 2009-2012

A chemical reaction scheme shows two reactants on the left, an arrow with "Pd(0)" above it, and a product on the right. Below the product is the text "68-100% de".

5. Asymmetric synthesis of an axially chiral antimitotic biaryl via an atropo-enantioselective Suzuki cross-coupling
A. Herrbach, A. Marinetti, O. Baudoin, D. Guénard, F. Guéritte, J. Org. Chem. 2003, 68, 4897-4905

A chemical reaction scheme shows two reactants, a benzene ring with an amino group and a B(pin) group, and a benzene ring with an iodine atom and a C(ethyl)2CH2OMOM group. An arrow points to the product, a complex ring structure with an aR label, with Pd(0)/L* written below the arrow.

4. Natural bridged biaryls with axial chirality and antimitotic properties
O. Baudoin, F. Guéritte, in Studies in Natural Product Chemistry, vol. 29 (Ed.: Atta-Ur-Rahman), Elsevier, 2003, 355-418

2002

3. Synthesis and biological evaluation of A-ring biaryl-carbamate analogues of rhazinilam
O. Baudoin, F. Claveau, S. Thoret, A. Herrbach, D. Guénard, F. Guéritte, Bioorg. Med. Chem. 2002, 10, 3395-3400

A chemical structure diagram shows a molecule with a five-membered ring containing nitrogen and oxygen, fused to a six-membered ring. Another six-membered ring is attached to the five-membered ring. Two ethyl groups are attached to a carbon atom. An R group is attached to the fused six-membered ring.

2. Application of the palladium-catalyzed borylation/Suzuki coupling (BSC) reaction to the synthesis of biologically active biaryl-lactams
O. Baudoin, M. Cesario, D. Guénard, F. Guéritte, J. Org. Chem. 2002, 67, 1199-1207

A chemical reaction scheme shows two reactants on the left, an arrow with reaction conditions, and a product on the right. The first reactant is a benzene ring with NHR and X groups. The second reactant is a benzene ring with CH2CN and X groups. The reaction conditions are 1) BSC reaction, 2) aq. NaOH. The product is a tricyclic compound with two benzene rings fused to a seven-membered ring containing a carbonyl and an NH group.

2000

1.  Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2’-disubstituted biphenyls
O. Baudoin, D. Guénard, F. Guéritte, J. Org. Chem.  2000, 65, 9268-9271

A chemical reaction scheme shows 2-bromoaniline reacting with 2-iodophenylacetonitrile, which has R1 and R2 substituents, in a two-step process: 1) Pd-catalyzed borylation, 2) Suzuki coupling. The product is 2-aminobiphenyl with a cyanomethyl group substituted with R1 and R2.
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