cs6b01914_si_001.pdf (1.89 MB)
Light-Mediated Reductive Debromination of Unactivated Alkyl and Aryl Bromides
journal contribution
posted on 2016-07-14, 00:00 authored by James J. Devery, John D. Nguyen, Chunhui Dai, Corey R. J. StephensonCleavage
of carbon–halogen bonds via either single-electron reduction
or atom transfer is a powerful transformation in the construction
of complex molecules. In particular, mild, selective hydrodehalogenations
provide an excellent follow-up to the application of halogen atoms
as directing groups or the utilization of atom transfer radical addition
(ATRA) chemistry for the production of hydrocarbons. Here we combine
the mechanistic properties of photoredox catalysis and silane-mediated
atom transfer chemistry to accomplish the hydrodebromination of carbon–bromide
bonds. The resulting method is performed under visible light irradiation
in an open vessel and is capable of the efficient reduction of a variety
of unactivated alkyl and aryl substrates.