Copper-Catalyzed Hydrative Amide Synthesis with Terminal Alkyne, Sulfonyl Azide, and Water

详细信息    查看全文

• 作者：Seung Hwan Cho ; Eun Jeong Yoo ; Imhyuck Bae ; and Sukbok Chang
• 刊名：Journal of the American Chemical Society
• 出版年：2005
• 出版时间：November 23, 2005
• 年：2005
• 卷：127
• 期：46
• 页码：16046 - 16047
• 全文大小：59K
• 年卷期：v.127,no.46(November 23, 2005)
• ISSN：1520-5126

文摘

It is shown for the first time that N-sulfonyl amides can be efficiently prepared by an unconventional approach of the hydrative reaction between terminal alkynes, sulfonyl azides, and water in the presence of copper catalyst and amine base under very mild conditions. The present route is quite general, and a wide range of alkynes and sulfonyl azides are readily coupled catalytically with water to furnish amides in high yields. A variety of labile functional groups are tolerated under the conditions, and the reaction is regioselective in that only terminal alkynes react while double or internal triple bonds are intact. The reaction can be readily scaled up and is also adaptable to a solid-phase procedure with high efficiency.