Arylthio-Metal Exchange of α-Arylthioalkanenitriles

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• 作者：Dinesh Nath ; Melanie C. Skilbeck ; Iain Coldham ; Fraser F. Fleming
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：January 3, 2014
• 年：2014
• 卷：16
• 期：1
• 页码：62-65
• 全文大小：322K
• ISSN：1523-7052

文摘

The addition of BuLi, Bu₃MgLi, Et₂ZnBuLi, or Me₂CuLi to 伪-arylthioalkanenitriles triggers an arylthio-metal exchange. NMR spectroscopic analyses implicate organometallic attack on sulfur forming a three-coordinate sulfidate as the key intermediate. Electrophilic trapping affords tertiary and quaternary nitriles in high yield. The method addresses the challenge of improving the functional group tolerance and preventing polyalkylations.