Reductive electrophilic C–H alkylation of quinolines by a reusable iridium nanocatalyst. Issue 41 (30th September 2021)

• Record Type: Journal Article
• Authors: Xie, Rong; Mao, Wenhui; Jia, Huanhuan; Sun, Jialu; Lu, Guangpeng; Jiang, Huanfeng; Zhang, Min
• Is Part Of: Chemical science. Volume 12:Issue 41(2021)
• Page Start: 13802
• Page End: 13808
• Publication Date: 2021-09-30
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d1sc02967c
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : By developing a heterogeneous iridium catalyst composed of a N-doped SiO2 /TiO2 support and Ir-species (Ir/N-SiO2 /TiO2 ), its application in reductive electrophilic alkylation of quinolines with various aryl carbonyls or benzyl alcohols is presented. Abstract : 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 δ + ) 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.