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Photoredox Activation of SF 6 for Fluorination
Author(s) -
McTeague T. Andrew,
Jamison Timothy F.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201608792
Subject(s) - chemoselectivity , allylic rearrangement , reagent , inert , photoredox catalysis , chemistry , catalysis , flow chemistry , fluoride , combinatorial chemistry , halogenation , functional group , organic chemistry , photochemistry , nanotechnology , materials science , inorganic chemistry , photocatalysis , polymer
We report the first practical use of SF 6 as a fluorinating reagent in organic synthesis. Photoredox catalysis enables the in situ conversion of SF 6 , an inert gas, into an active fluorinating species by using visible light. Under these conditions, deoxyfluorination of allylic alcohols is effected with high chemoselectivity and is tolerant of a wide range of functional groups. Application of the methodology in a continuous‐flow setup achieves comparable yields to those obtained with a batch setup, while providing drastically increased material throughput of valuable allylic fluoride products.