Litcius/Paper detail

Visible-Light-Induced α-Arylation of Ketones with (Hetero)aryl Halides

Chuyun Liang, Shuzhong Wang, Yunhao Xue, Xiaohui He, Jialiang Qin, Ruoting Zhan, Bo Liu, Huicai Huang

2024Organic Letters9 citationsDOI

Abstract

An enamine-mediated photoredox catalyzed C(sp 2 )–C(sp 3 ) cross-coupling of dual radical precursors for the arylation of ketone is presented in this Letter. These reactions led to the formation of an enamine by using pyrrolidine to functionalize the C(sp 3 )–H bond in ketone substrates, which could be smoothly converted to α-arylated ketones with inert aryl bromides and even aryl chlorides in moderate to good yields under mild reaction conditions. The photocatalytically induced C(sp 2 )–C(sp 3 ) cross-coupling between unactivated noncyclic ketones and aryl halides was achieved, and multiple carbonyl α-arylated backbones containing various natural products and drug molecules were successfully constructed.

Topics & Concepts

HalideChemistryArylCombinatorial chemistryAryl halideVisible spectrumPhotochemistryOrganic chemistryAlkylOptoelectronicsPhysicsRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods