Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 6, Issue 10, Pages 2618-2634Publisher
WILEY-BLACKWELL
DOI: 10.1002/asia.201100340
Keywords
alkynes; click chemistry; copper; ketenimines; multicomponent reactions
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Funding
- Korea Research Foundation [KRF-2008-C00024]
- MIRC [NRF-2010-0001957]
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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.
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