Palladium-catalyzed direct alkynylation of N-vinylacetamides

• Main Authors: Loh, Teck-Peng, Xu, Yun-He, Zhang, Qiu-Chi, He, Tao, Meng, Fei-Fan
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2014
• Subjects: DRNTU::Science::Chemistry
• Online Access: https://hdl.handle.net/10356/101116; http://hdl.handle.net/10220/19714
• Institution: Nanyang Technological University

A direct ethynylation reaction between N-vinylacetamides and (bromoethynyl)triisopropylsilane catalyzed by palladium is reported. A broad scope of cyclic N-vinylacetamide derivatives was tolerated and the corresponding products could be obtained in acceptable yields. This work provides a general tool for the synthesis of conjugated enyne products using palladium(II) acetate as catalyst. The mild reaction conditions and reasonable results should make this method a useful synthetic protocol. Unfortunately, other bromo-substituted alkynes are found to be unreactive and could not afford the desired products under the current reaction conditions.