Work

Metallaphotoredox Perfluoroalkylation of Organobromides

Year: 2020

Type: article

Abstract: ) are readily available, air-stable, and easy-to-handle fluoroalkyl sources. Herein, we describe a mild, copper-catalyzed cross-coupling of these fluoroalkyl nucleophiles with aryl and alkyl bromides to produce a diverse array of trifluoromethyl, pentafluoroethyl, and heptafluoropropyl adducts. This light-mediated transformation proceeds via a silyl-radical-mediated halogen atom abstraction pathway, which enables perfluoroalkylation of a broad range of organobromides of variable steric and electronic demand. The utility of the method is demonstrated through the late-stage functionalization of several drug analogues.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.0c09977

Authors: Xiangbo Zhao, David W. C. MacMillan

Institution: Princeton University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Princeton University, National Institute of General Medical Sciences

Award: Photoredox Catalysis Applications in Organometallics and Chemical Biology