Synthesis of Internal Alkynes through an Effective Tandem Elimination–Hydrodebromination–Cross-Coupling of gem-Dibromoalkenes with HalobenzenesThis 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.
Received: 17 June 2017
Accepted after revision: 24 August 2017
14 September 2017 (eFirst)
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.