Reductive electrophilic C-H alkylation of quinolines by a reusable iridium nanocatalyst

The incorporation of a coupling step into the reduction of unsaturated systems offers a desirable way for diverse synthesis of functional molecules, but it remains to date a challenge due to the difficulty in controlling the chemoselectivity. Herein, by developing a new heterogeneous iridium catalyst composed of Ir-species (Ir delta+) and N-doped SiO2/TiO2 support (Ir/N-SiO2/TiO2), we describe its application in reductive electrophilic mono and dialkylations of quinolines with various 2- or 4-functionalized aryl carbonyls or benzyl alcohols by utilizing renewable formic acid as the reductant. This catalytic transformation offers a practical platform for direct access to a vast range of alkyl THQs, proceeding with excellent step and atom-efficiency, good substrate scope and functional group tolerance, a reusable catalyst and abundantly available feedstocks, and generation of water and carbon dioxide as by-products. The work opens a door to further develop more useful organic transformations under heterogeneous reductive catalysis.

Automated summary

The development of a new heterogeneous iridium catalyst has allowed for the successful reductive electrophilic reactions of quinolines with various functionalized compounds using renewable formic acid as the reductant, showcasing high efficiency, broad substrate scope, and environmentally friendly characteristics.