Organic Chemistry Portal



Palladium-Catalyzed Coupling of Terminal Alkynes with Benzyl Ammonium Salts

Silin Xu, Zhenming Zhang, Chunyu Han, Wenkai Hu, Tiwen Xiao, Yanan Yuan and Junfeng Zhao*

*College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, People's Republic of China, Email:

S. Xu, Z. Zhang, C. Han, W. Hu, T. Xiao, Y. Yuan, J. Zhao, J. Org. Chem., 2019, 84, 12157-12164.

DOI: 10.1021/acs.joc.9b01877

see article for more reactions


A highly efficient palladium-catalyzed Sonogashira coupling of benzylic ammonium salts with terminal alkynes provides a series of internal alkyne derivatives in good yields. The reaction offers a broad substrate scope and high functional group tolerance.

see article for more examples

proposed mechanism

Key Words

benzylation, alkynylation, Sonogashira coupling

ID: J42-Y2019