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Silver(I)‐Catalyzed N ‐Trifluoroethylation of Anilines and O ‐Trifluoroethylation of Amides with 2,2,2‐Trifluorodiazoethane
Author(s) -
Luo Haiqing,
Wu Guojiao,
Zhang Yan,
Wang Jianbo
Publication year - 2015
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.201507219
Subject(s) - carbene , catalysis , chemistry , medicinal chemistry , combinatorial chemistry , silver salts , reaction conditions , organic chemistry
A straightforward N‐trifluoroethylation of anilines has been developed based on silver‐catalyzed NH insertions with 2,2,2‐trifluorodiazoethane (CF 3 CHN 2 ). Mechanistically, the reaction is proposed to involve migratory insertion of a silver carbene as the key step. In contrast, when amides are employed as the substrates under similar reaction conditions, O‐trifluoroethylation occurs to afford trifluoroethyl imidates.