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Palladium/Copper-Catalyzed Oxidative Arylation of Terminal Alkenes with Aroyl Hydrazides

Authors

  • Yong-Gang Zhang,

    1. Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (P. R. China), Fax: (+86) 551-63601592
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  • Xiang-Lei Liu,

    1. Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (P. R. China), Fax: (+86) 551-63601592
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  • Zeng-Yang He,

    1. Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (P. R. China), Fax: (+86) 551-63601592
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  • Xi-Ming Li,

    1. Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (P. R. China), Fax: (+86) 551-63601592
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  • Hong-Jian Kang,

    1. Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (P. R. China), Fax: (+86) 551-63601592
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  • Prof. Dr. Shi-Kai Tian

    Corresponding author
    1. Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (P. R. China), Fax: (+86) 551-63601592
    2. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032 (P. R. China)
    • Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (P. R. China), Fax: (+86) 551-63601592

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Abstract

An unprecedented oxidative arylation reaction of terminal alkenes with simple aroyl hydrazides has been developed under aerobic conditions for the stereoselective synthesis of 1,2-disubstituted alkenes. A range of aroyl hydrazides underwent palladium/copper-catalyzed oxidative Mizoroki–Heck reaction with terminal alkenes open to air in a 1:1 mixture of dimethyl sulfoxide and acetonitrile to give structurally diverse 1,2-disubstituted alkenes in moderate to excellent yields with excellent regio- and E-selectivity. The reaction tolerated a wide variety of functional groups, such as alkoxy, hydroxy, amino, fluoro, chloro, bromo, cyano, nitro, ester, amide, imide, phosphine oxide, and sulfone groups, and, moreover, molecular oxygen and dimethyl sulfoxide were demonstrated to serve as terminal oxidants. This study provides a useful method for the stereoselective synthesis of 1,2-disubstituted alkenes through direct transformation of the vinylic C[BOND]H bonds in terminal alkenes.

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