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Photoredox Generation of Carbon‐Centered Radicals Enables the Construction of 1,1‐Difluoroalkene Carbonyl Mimics
Author(s) -
Lang Simon B.,
Wiles Rebecca J.,
Kelly Christopher B.,
Molander Gary A.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201709487
Subject(s) - trifluoromethyl , radical , alkene , chemistry , reagent , alkylation , functional group , primary (astronomy) , combinatorial chemistry , carbon fibers , photochemistry , organic chemistry , catalysis , materials science , alkyl , polymer , physics , astronomy , composite number , composite material
Described is a facile, scalable route to access functional‐group‐rich gem ‐difluoroalkenes. Using visible‐light‐activated catalysts in conjunction with an arsenal of carbon‐radical precursors, an array of trifluoromethyl‐substituted alkenes undergoes radical defluorinative alkylation. Nonstabilized primary, secondary, and tertiary radicals can be used to install functional groups in a convergent manner, which would otherwise be challenging by two‐electron pathways. The process readily extends to other perfluoroalkyl‐substituted alkenes. In addition, we report the development of an organotrifluoroborate reagent to expedite the synthesis of the requisite trifluoromethyl‐substituted alkene starting materials.