Research

The functionalization of carbon–hydrogen bonds offers an attractive step-economical entry into valuable organic intermediates from simple hydrocarbon precursors. The recent research of our group has focused on the development of various transition-metal-catalyzed methods for the functionalization of non-activated C(sp³)–H and C(sp²)–H bonds.

The reactions that we have developed allow the formation of C(sp³)–C(sp²) bonds from simple C(sp²)–X/C(sp³)–H precursors (X = leaving group) using palladium catalysts. A variety of valuable carbocycles and heterocycles are generated through these methods.

Review: Acc. Chem. Res. 2017, 50, 1114.

Leading papers: Angew. Chem. Int. Ed. 2003, 42, 5736; J. Am. Chem. Soc. 2008, 130, 15157; J. Am. Chem. Soc. 2010, 132, 10706; Angew. Chem. Int. Ed. 2012, 51, 10399; Angew. Chem. Int. Ed. 2016, 55, 2805; Angew. Chem. Int. Ed. 2017, 56, 7218; Angew. Chem. Int. Ed. 2018, 57, 12131.

Recently, we employed the 1,4-Pd shift strategy to reach more distant C(sp³)–H bonds and create both C(sp²)–C(sp³) and C(sp³)–C(sp³) bonds.

Leading papers: Org. Lett. 2019, 21, 1434; Angew. Chem. Int. Ed. 2019, 58, 14625; J. Am. Chem. Soc. 2020, 142, 15355; Angew. Chem. Int. Ed. 2020, 59, 18980.

We are developing enantioselective C(sp³)–H and C(sp²)–H activation reactions using various types of chiral catalysts. These methods allow access to enantioenriched molecules with potential applications in medicinal chemistry or chiroptical devices.

Review: Chem. Eur. J.  2021, 27, 1231.

Leading papers: ACS Catal. 2015, 5, 4300; Angew. Chem. Int. Ed. 2017, 56, 7218; Chem. Sci.  2017, 8, 1344; Angew. Chem. Int. Ed. 2018, 57, 1394; J. Am. Chem. Soc. 2020, 142, 2161;Angew. Chem. Int. Ed. 2021, 60, 5136; Angew. Chem. Int. Ed. 2021, 60, 7245.

Multiple C–H activation allows to streamline the synthesis of bioactive natural products using simpler precursors. Using such strategies, we recently synthesized:

- aeruginosins (e. g., aeruginosin 298A), cyanotoxins isolated from various blue-green algae;
- lycorine alkaloids, originated from Amaryllidaceae plants (e. g., γ-lycorane);
- (nor)illudalane sesquiterpenes (e. g., puraquinonic acid and russujaponol F), isolated from various species of higher fungi;
- pentacyclic dithiodiketopiperazines (e. g., epicoccin G and rostratin A), isolated from various types of fungi.

Review: Angew. Chem. Int. Ed. 2020, 59, 17798.

Leading papers: Angew. Chem. Int. Ed. 2015, 54, 4919; Org. Lett. 2018, 20, 772; Org. Lett. 2019, 21, 812; J. Am. Chem. Soc. 2019, 141, 15779.