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Synthesis of Internal Alkynes through an Effective Tandem Elimination-Hydrodebromination-Cross-Coupling of gem-Dibromoalkenes with Halobenzenes

Yuan Ji, Ning Zhong, Zinan Kang, Guobing Yan*, Ming Zhao*

*Department of Chemistry, Lishui University, Lishui 323000; School of Chemical Engineering, China University of Mining and Technology, Xuzhou 221116, P. R. of China, Email: gbyanlsu.edu.cn, ming815zhaoaliyun.com

Y. Ji, N. Zhong, Z. Kang, G. Yan, M. Zhao, Synlett, 2018, 29, 209-214.

DOI: 10.1055/s-0036-1590907 (free Supporting Information)


Abstract

A palladium-catalyzed C-C cross-coupling reaction of gem-dibromoalkenes and halobenzenes provides terminal alkynes in one pot through a tandem elimination-hydrodebromination process. This convenient reaction proceeded under copper-free Sonogashira coupling reaction conditions in good to excellent yields.

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Key Words

internal alkynes, dibromoalkenes, halobenzenes, alkynylations, Sonogashira coupling, palladium catalysis, C-C coupling


ID: J60-Y2018