Litcius/Paper detail

Decarboxylative C–H silylation of N-heteroarenes with silanecarboxylic acids

Guodong Zhang, Ye Tian, Chengyu Zhang, Xiang Li, Feng Chen

2023Chemical Communications27 citationsDOI

Abstract

Established decarboxylative Minisci reactions are limited to aliphatic carboxylic acids, as their analogs, silanecarboxylic acids, have been rarely investigated. Herein, we present a new decarboxylative Minisci-type reaction of N-heteroarenes with silanecarboxylic acids under photo- or silver-mediated conditions. This C-H silylation strategy provides efficient access to diverse N-heteroarylsilanes in moderate to excellent yields with high regioselectivity, among which Ag-catalysed decarboxylation of silanecarboxylic acids furnishes an unprecedented method for silyl radical generation.

Topics & Concepts

SilylationChemistryMedicinal chemistryStereochemistryOrganic chemistryCatalysisCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesRadical Photochemical Reactions
Decarboxylative C–H silylation of N-heteroarenes with silanecarboxylic acids | Litcius