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Copper(I)‐Catalyzed Regioselective Chan‐Lam N 2‐Vinylation of 1,2,3‐Triazoles and Tetrazoles
Author(s) -
Motornov Vladimir,
Latyshev Gennadij V.,
Kotovshchikov Yury N.,
Lukashev Nikolay V.,
Beletskaya Irina P.
Publication year - 2019
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.201900225
Subject(s) - chemistry , regioselectivity , catalysis , copper , selectivity , base (topology) , medicinal chemistry , combinatorial chemistry , salt (chemistry) , coupling (piping) , organic chemistry , mathematical analysis , mathematics , mechanical engineering , engineering
Copper‐catalyzed coupling of π‐deficient NH‐azoles with vinylboronic acids or vinyltrifluoroborate salt provides a direct route to N2 ‐vinyl‐1,2,3‐triazoles and N2 ‐vinyltetrazoles. The coupling reaction is efficiently catalyzed by (phen)Cu(PPh 3 )Br with low catalyst loading (5 mol%) under base‐free conditions. The method is applicable for vinylation of unsubstituted, monosubstituted, and disubstituted 1,2,3‐triazoles with various functionalities with high N2 ‐selectivity.