Benzannulation of Triynes Initiated by an Alder-Ene Reaction and Subsequent Trifluoromethylthiolate Addition

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• 作者：Rajdip Karmakar ; Phani Mamidipalli ; Ryan M. Salzman ; Seongwon Hong ; Sang Young Yun ; Wei Guo ; Yuanzhi Xia ; Daesung Lee
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：August 5, 2016
• 年：2016
• 卷：18
• 期：15
• 页码：3530-3533
• 全文大小：393K
• 年卷期：0
• ISSN：1523-7052

文摘

A new benzannulation reaction with accompanied trifluoromethylthiolation is described. This benzannulation can generate a range of trifluoromethylthiolated benzolactams and benzolactones from 1,3,8-triynes and a stoichiometric amount of AgSCF₃ at 90 °C through an initial Alder-ene reaction, 1,4-addition of AgSCF₃, and a series of bond-reorganization processes that include double bond migration, 6π-electrocyclization, and a [1,3]-H shift. For certain substrates containing a triisopropylsilyl (TIPS) group, the final [1,3]-H shift-interrupted products, were obtained.