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Synthesis of E-Alkyl Alkenes from Terminal Alkynes via Ni-Catalyzed Cross-Coupling of Alkyl Halides with B-Alkenyl-9-borabicyclo[3.3.1]nonanes

Thomas Di Franco, Alexandre Epenoy and Xile Hu*

*Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne (EPFL), 1015 Lausanne, Switzerland, Email: xile.huepfl.ch

T. Di Franco, A. Epenoy, X. Hu, Org. Lett., 2015, 17, 4910-4913.

DOI: 10.1021/acs.orglett.5b02482 (free Supporting Information)


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Abstract

A Ni-catalyzed Suzuki-Miyaura coupling of primary and secondary alkyl halides including alkyl chlorides with alkenyl-(9-BBN) reagents allows - also in combination with one pot hydroboration of terminal alkynes - the expedited synthesis of functionalized alkyl alkenes from readily available alkynes with complete (E)-selectivity.

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Key Words

alkenes, Suzuki Coupling


ID: J54-Y2015