C(sp<sup>3</sup>)–H Carboxylation via Carbene/Photoredox Cooperative Catalysis
Cullen R. Schull, Jing Cao, Sophia R. Mitton-Fry, Mara Mrksich, Karl A. Scheidt
Abstract
C(sp 3 )–H bond functionalization is a powerful strategy for the synthesis of organic compounds due their abundance in simple starting materials. Photoredox catalysis has led to a diverse array of enabling C(sp 3 )–H activation strategies; however, a general platform for the direct functionalization of C(sp 3 )–H to carboxylic acid derivatives remains elusive. Disclosed herein is the development of a cooperative NHC/photoredox-catalyzed C(sp 3 )–H esterification transformation. This method enables access to benzylic, α-heteroatom, and formal β-esterification products in moderate to high yields under mild reaction conditions.
Topics & Concepts
CarboxylationSurface modificationPhotoredox catalysisCarbeneCatalysisChemistryCombinatorial chemistryHeteroatomOrganocatalysisOrganic chemistryPhotochemistryEnantioselective synthesisPhotocatalysisRing (chemistry)Physical chemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques