Site‐Selective Tertiary Alkyl–Fluorine Bond Formation from α‐Bromoamides Using a Copper/CsF Catalyst System | Zendy

Nishikata Takashi | Zendy; Ishida Syo | Zendy; Fujimoto Ryo | Zendy

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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

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201603426

Subject(s) - alkyl , chemistry , reagent , catalysis , copper , amide , radical , fluorine , primary (astronomy) , organic chemistry , salt (chemistry) , polymer chemistry , medicinal 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.

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