Publications

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, doi.org/10.1002/chem.202103467.

 

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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, https://doi.org/10.1002/anie.202110019.

 

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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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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

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

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

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

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

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

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

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

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

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

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

2015

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

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

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

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

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

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

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

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

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

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

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

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

2012

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

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

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

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

2011

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

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")

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)

2009

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

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

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

2008

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

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

17. Synthesis of tubulin-binding bridged biaryls via intermolecular Suzuki coupling
O. Baudoin, C. R. Chimie2008, 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

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

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

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

2005

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

2004

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

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

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

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

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

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