Synlett
DOI: 10.1055/s-0036-1590907
letter
© Georg Thieme Verlag Stuttgart · New York

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

Yuan Jia, Ning Zhonga, Zinan Kanga, Guobing Yan*b, Ming Zhao*a
  • aSchool of Chemical Engineering, China University of Mining and Technology, No. 1 Daxue Road, Xuzhou 221116, P. R. of China
  • bDepartment of Chemistry, Lishui University, Lishui 323000, P. R. of China   Email: ming815zhao@aliyun.com   Email: gbyan@lsu.edu.cn
This work was supported by Fundamental Research Funds for the Central Universities (No. 2015XKMS048), the Natural Science Foundation of Jiangsu Province (No. BK20160254), the National Natural Science Foundation of China (No. 21572094), and A Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions.
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Publication History

Received: 17 June 2017

Accepted after revision: 24 August 2017

Publication Date:
14 September 2017 (eFirst)

Abstract

Carbon–carbon couplings are among the most important strategies for constructing functional molecules in organic synthetic chemistry, and cheap, diverse, and readily available coupling partners are crucial to these diverse reactions. In this contribution, we report the first palladium-catalyzed C–C cross-coupling reaction of two kinds of organic halide, a gem-dibromoalkene and a halobenzene, as the starting materials. Terminal alkynes were generated in situ through a tandem elimination–hydrodebromination process, and the internal alkyne final products were synthesized in one pot. The reaction proceeded under simple, facile, and classic copper-free Sonogashira coupling reaction conditions in good to excellent yields.

Supporting Information