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Deoxyfluorination with CuF 2 : Enabled by Using a Lewis Base Activating Group
Author(s) -
Sood D. Eilidh,
Champion Sue,
Dawson Daniel M.,
Chabbra Sonia,
Bode Bela E.,
Sutherland Andrew,
Watson Allan J. B.
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202001015
Subject(s) - bespoke , adduct , reactivity (psychology) , fluoride , chemistry , reagent , nucleophile , lewis acids and bases , base (topology) , transition metal , group (periodic table) , metal , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , inorganic chemistry , medicine , mathematical analysis , alternative medicine , mathematics , pathology , political science , law
Deoxyfluorination is a primary method for the formation of C−F bonds. Bespoke reagents are commonly used because of issues associated with the low reactivity of metal fluorides. Reported here is the development of a simple strategy for deoxyfluorination, using first‐row transition‐metal fluorides, and it overcomes these limitations. Using CuF 2 as an exemplar, activation of an O‐alkylisourea adduct, formed in situ, allows effective nucleophilic fluoride transfer to a range of primary and secondary alcohols. Spectroscopic investigations have been used to probe the origin of the enhanced reactivity of CuF 2 . The utility of the process in enabling 18 F‐radiolabeling is also presented.