Metal-Free Markovnikov-Type Alkyne Hydration under Mild Conditions

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• 作者：Wenbo Liu ; Haining Wang ; Chao-Jun Li
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：May 6, 2016
• 年：2016
• 卷：18
• 期：9
• 页码：2184-2187
• 全文大小：272K
• 年卷期：0
• ISSN：1523-7052

文摘

A Markovnikov-type alkyne hydration protocol is presented using 20% CF₃SO₃H (TfOH) as the catalyst under unprecedented mild conditions applicable to various alkynes, including terminal arylalkynes, terminal nonfunctionalized aliphatic alkynes, and internal alkynes with excellent regioselectivity in good to excellent yields (average yields >85%). The reaction procedure operates under mild conditions (25–70 °C), with broad functional group compatibility, and uses only slightly more than a stoichiometric amount of water in the absence of any transition metal. The success of this protocol hinges upon the utilization of trifluoroethanol as the solvent.