Open AccessMetallaphotoredox Perfluoroalkylation of Organobromides
Author(s) -
Xiangbo Zhao,
David W. C. MacMillan
Publication year - 2020
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.0c09977
Subject(s) - chemistry , trifluoromethyl , nucleophile , silylation , adduct , aryl , steric effects , halogen , reagent , combinatorial chemistry , alkyl , organic chemistry , catalysis
Ruppert-Prakash type reagents (TMSCF 3 , TMSC 2 F 5 , and TMSC 3 F 7 ) 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.