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Silver‐Mediated N ‐Trifluoromethylation of Amides and Peptides
Author(s) -
Zhang Zhenzhen,
He Jiayan,
Zhu Lin,
Xiao Haiwen,
Fang Yewen,
Li Chaozhong
Publication year - 2020
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202000132
Subject(s) - trifluoromethylation , chemistry , selectfluor , combinatorial chemistry , reaction conditions , stereochemistry , organic chemistry , trifluoromethyl , reagent , catalysis , alkyl
Summary of main observation and conclusion We report herein the direct N ‐trifluoromethylation of N ‐H amides. Promoted by AgOTf and 2‐fluoropyridine, the reaction of a variety of amides with Selectfluor, TMSCF 3 and CsF proceeds smoothly at room temperature leading to the corresponding N ‐trifluoromethylated products in satisfactory yields. The protocol is also applicable to amino acid derivatives, resulting in efficient and chemoselective N ‐trifluoromethylation of di‐ and tri‐peptides with retention of configuration. A mechanism involving reductive elimination of Ag(III) intermediates to form N—CF 3 bonds is proposed.