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1,3‐Difunctionalization of Imino‐Carbenes via Rhodium‐Catalyzed Reactions of Triazoles with Acyl Selenides
Author(s) -
Li Fang,
Pei Chao,
Quaranta Calogero,
Koenigs Rene M.
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100629
Subject(s) - chemistry , rhodium , catalysis , stereoselectivity , ylide , yield (engineering) , combinatorial chemistry , reaction conditions , functional group , insertion reaction , organic chemistry , materials science , polymer , metallurgy
Herein, we report on the rhodium‐catalyzed reaction of triazoles with acyl selenides. Under thermal reaction conditions and in the presence of a rhodium catalyst, a rapid 1,3‐difunctionalization reaction occurs to provide valuable α‐seleno enamides with high stereoselectivity and broad functional group tolerance, which was demonstrated in 35 examples with up to 95% yield. Computational calculations suggest a reaction pathway that gives a direct access to the 1,3‐difunctionalization without intermittent formation of ylide intermediates.