Preparation of 1,5-Disubstituted 1,2,3-Triazoles via Ruthenium-catalyzed Azide Alkyne Cycloaddition.
作者信息
Oakdale James S, Fokin Valery V, Umezaki Satoshi, Fukuyama Tohru
出版信息
Organic Synth. 2013 Jan 1;90:96-104. doi: 10.15227/orgsyn.090.0096.
Abstract
摘要
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3
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Chemistry. 2009;15(8):1929-38. doi: 10.1002/chem.200801563.
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