Litcius/Paper detail

Organoelectrophotocatalytic C–H Silylation of Heteroarenes

Qinhui Wan, Zhong‐Wei Hou, Xin‐Ru Zhao, Xiaoyu Xie, Lei Wang

2023Organic Letters84 citationsDOI

Abstract

An organoelectrophotocatalytic approach for the C–H silylation of heteroarenes through dehydrogenation cross-coupling with H 2 evolution has been developed. The organoelectrophotocatalytic strategy is carried out under a simple and efficient monocatalytic system by employing 9,10-phenanthrenequinone both as an organocatalyst and as a hydrogen atom transfer (HAT) reagent, which avoids the need for an external HAT reagent, an oxidant, or a metal reagent. A variety of heteroarenes can be compatible in satisfactory yields with excellent regioselectivity.

Topics & Concepts

ChemistryReagentDehydrogenationSilylationRegioselectivityCombinatorial chemistryHydrogen atomOrganic chemistryCatalysisGroup (periodic table)Radical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques