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Copper‐Catalyzed Synthesis of N ‐Sulfonyl‐1,2,3‐triazoles: Controlling Selectivity
Author(s) -
Yoo Eun Jeong,
Ahlquist Mårten,
Kim Seok Hwan,
Bae Imhyuck,
Fokin Valery V.,
Sharpless K. Barry,
Chang Sukbok
Publication year - 2007
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.200604241
Subject(s) - sulfonyl , ketenimine , cycloaddition , catalysis , selectivity , chemistry , azide , combinatorial chemistry , copper , alkyne , medicinal chemistry , organic chemistry , alkyl
4‐Substituted 1‐( N ‐sulfonyl)‐1,2,3‐triazoles are selectively obtained by using the Cu‐catalyzed azide–alkyne cycloaddition reaction with sulfonyl azides. Performing the reaction at 0 °C in chloroform in the presence of 2,6‐lutidine and CuI as the catalyst effectively prevents the ketenimine pathway and provides convenient access to N ‐sulfonyltriazoles in good to excellent yields.