Selective Intermolecular Oxidative Cross-Coupling of Enolates

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• 作者：Toru Amaya ; Yusuke Maegawa ; Takaya Masuda ; Yuma Osafune ; Toshikazu Hirao
• 刊名：Journal of the American Chemical Society
• 出版年：2015
• 出版时间：August 19, 2015
• 年：2015
• 卷：137
• 期：32
• 页码：10072-10075
• 全文大小：413K
• ISSN：1520-5126

文摘

Selective intermolecular oxidative cross-coupling of enolates, which is a bond-forming reaction between carbanion equivalents, remains as an unsolved issue despite its potential utility for the direct synthesis of unsymmetrical 1,4-diones. The main difficulty derives from the unavoidable homo-coupling. Our strategy depends on the selective one-electron oxidation of one enolate to afford an electrophilic carbonyl 伪-radical species, followed by trapping with another enolate. The present study demonstrates the selective oxovanadium(V)-induced cross-coupling between boron and silyl enolates.