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Site‐Selective Tertiary Alkyl–Fluorine Bond Formation from α‐Bromoamides Using a Copper/CsF Catalyst System
Author(s) -
Nishikata Takashi,
Ishida Syo,
Fujimoto Ryo
Publication year - 2016
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.201603426
Subject(s) - alkyl , reagent , copper , catalysis , chemistry , fluorine , amide , radical , primary (astronomy) , salt (chemistry) , organic chemistry , polymer chemistry , physics , astronomy
A copper‐catalyzed site‐selective fluorination of α‐bromoamides possessing multiple reaction sites, such as primary and secondary alkyl−Br bonds, using inexpensive CsF is reported. Tertiary alkyl−F bonds, which are very difficult to synthesize, can be formed by this fluorination reaction with the aid of an amide group. Control experiments revealed that in situ generated CuF 2 is a key fluorinating reagent that reacts with the tertiary alkyl radicals generated by the reaction between an α‐bromocarbonyl compound and a copper(I) salt.