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Z-Selective Olefin Synthesis via Iron-Catalyzed Reductive Coupling of Alkyl Halides with Terminal Arylalkynes

Chi Wai Cheung, Fedor E. Zhurkin and Xile Hu*

*Laboratory of Inorganic Synthesis and Catalysis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), ISIC-LSCI, BCH 3305, Lausanne 1015, Switzerland, Email: xile.huepfl.ch

C. W. Cheung, F. E. Zhurkin, X. Hu, J. Am. Chem. Soc., 2015, 137, 4932-4935.

DOI: 10.1021/jacs.5b01784 (free Supporting Information)


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Abstract

A method to produce 1,2-disubstituted olefins in high Z selectivity via reductive cross-coupling of alkyl halides with terminal arylalkynes employs inexpensive and nontoxic catalyst (iron(II) bromide) and reductant (zinc). The substrate scope encompasses primary, secondary, and tertiary alkyl halides, and the reaction tolerates a large number of functional groups.

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Key Words

alkenes, Zinc


ID: J48-Y2015