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Sulfonyl and Phosphoryl Azides: Going Further Beyond the Click Realm of Alkyl and Aryl Azides
Author(s) -
Kim Seok Hwan,
Park Sae Hume,
Choi Ji Ho,
Chang Sukbok
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201100340
Subject(s) - ketenimine , chemistry , nucleophile , alkyl , sulfonyl , aryl , triazole , ring (chemistry) , click chemistry , selectivity , reactivity (psychology) , organic chemistry , combinatorial chemistry , azide , catalysis , medicinal chemistry , medicine , alternative medicine , pathology
Whereas alkyl and aryl azides readily react with terminal alkynes to afford 1,4‐disubstituted‐1,2,3‐triazoles in excellent yields and selectivity in the presence of a copper catalyst, sulfonyl, phosphoryl, and certain acyl azides allow additional chemistry upon ring‐opening of the corresponding copper–triazole intermediates. The amazingly versatile new chemistry stems from the high reactivity of a ring‐opened ketenimine intermediate, with which a wide range of nucleophiles react to give multicomponent products. Among those nucleophiles, amines, alcohols, water, and heterocyclic compounds are especially capable of being involved in this new chemistry.