Facile Synthesis of Disubstituted Isoxazoles from Homopropargylic Alcohol via C═N Bond Formation
Organic Letters2014Vol. 16(24), pp. 6298–6301
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Pin Gao, Hongxia Li, Xin‐Hua Hao, Dong‐Po Jin, Dao-Qian Chen, Xiao‐Biao Yan, Xin‐Xing Wu, Xian‐Rong Song, Xue‐Yuan Liu, Yong‐Min Liang
Abstract
A novel iron-catalyzed aerobic oxidative reaction to synthesize disubstituted isoxazoles from homopropargylic alcohol, t-BuONO, and H2O is developed. The method provides mild conditions to afford a variety of useful substituted heterocycles in an efficient and regioselective manner. The mechanism has been studied and proposed, which indicates that the transformation can be realized through construction of a C═N bond and C═O bond, C-H oxidation, and then cyclization. Moreover, this method can be enlarged to gram scale.
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