Open AccessCopper-Catalyzed C–H Fluorination/Functionalization Sequence Enabling Benzylic C–H Cross Coupling with Diverse Nucleophiles
Author(s) -
Aristidis Vasilopoulos,
Dung L. Golden,
Joshua A. Buss,
Shan S. Stahl
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c02238
Subject(s) - chemistry , nucleophile , electrophile , catalysis , medicinal chemistry , lewis acids and bases , electrophilic fluorination , combinatorial chemistry , surface modification , fluorine , hydrogen bond , fluoride , organic chemistry , molecule , inorganic chemistry
Site-selective transformation of benzylic C-H bonds into diverse functional groups is achieved via Cu-catalyzed C-H fluorination with N -fluorobenzenesulfonimide (NFSI), followed by substitution of the resulting fluoride with various nucleophiles. The benzyl fluorides generated in these reactions are reactive electrophiles in the presence of hydrogen-bond donors or Lewis acids, allowing them to be used without isolation in C-O, C-N, and C-C coupling reactions.