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Selective C(sp 3 )−H and C(sp 2 )−H Fluorination of Alcohols Using Practical Auxiliaries
Author(s) -
Mao YangJie,
Lou ShaoJie,
Hao HongYan,
Xu DanQian
Publication year - 2018
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.201808021
Subject(s) - chemistry , methylene , fluorine , halogenation , molecule , bond cleavage , organic chemistry , acetone , medicinal chemistry , catalysis
Selective introduction of fluorine into molecules by the cleavage of inert C−H bonds is of central academic and synthetic interest, yet remains challenging. Given the central role of alcohols in organic chemistry as the most ubiquitous building blocks, a versatile and selective C(sp 3 )−H and C(sp 2 )−H fluorination of simple alcohols, enabled by novel designed exo ‐directing groups, is described. C(sp 2 )−H bond fluorination was achieved by using a simple acetone oxime as auxiliary, whereas a new, modular and easily accessible bidentate auxiliary was developed for the efficient and site‐selective fluorination of various primary methyl, methylene, and benzylic C(sp 3 )−H bonds. Fluorinated alcohols can readily be accessed by the removal of auxiliaries, and significantly expands the synthetic prospect of the present procedure.