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  • Title: Directed Copper-Catalyzed Intermolecular Heck-Type Reaction of Unactivated Olefins and Alkyl Halides.
    Author: Tang C, Zhang R, Zhu B, Fu J, Deng Y, Tian L, Guan W, Bi X.
    Journal: J Am Chem Soc; 2018 Dec 12; 140(49):16929-16935. PubMed ID: 30421921.
    Abstract:
    A new type of intermolecular alkylative olefination of unactivated olefins and alkyl halides has been realized for the first time. This copper-promoted Heck-type reaction employs a directing-group strategy to efficiently produce the coupled alkyl olefin products with excellent regio- and stereoselectivity. A broad substrate scope including 1°, 2°, and 3° alkyl bromides and various nonactivated alkenes could be well tolerated. DFT calculations disclosed a dimethyl sulfoxide assisted concerted H-Br elimination process of a conformationally strained Cu(III) cyclic transition state.
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