Cyclopalladated Ferrocenylimine as Efficient Catalyst for the Syntheses of Arylboronate Esters

Authors

  • Lianhui Wang,

    1. Department of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, People's Republic of China, Fax: (+86)-371-6776-7753 (X.C.), (+86)-371-6776-6667 (Y.W.)
    2. Tetranov Biopharm, Inc.,Zhengzhou 450052, People's Republic of China
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  • Jingya Li,

    1. Tetranov Biopharm, Inc.,Zhengzhou 450052, People's Republic of China
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  • Xiuling Cui,

    1. Department of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, People's Republic of China, Fax: (+86)-371-6776-7753 (X.C.), (+86)-371-6776-6667 (Y.W.)
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  • Yusheng Wu,

    1. Tetranov Biopharm, Inc.,Zhengzhou 450052, People's Republic of China
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  • Zhiwu Zhu,

    1. Department of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, People's Republic of China, Fax: (+86)-371-6776-7753 (X.C.), (+86)-371-6776-6667 (Y.W.)
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  • Yangjie Wu

    1. Department of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, People's Republic of China, Fax: (+86)-371-6776-7753 (X.C.), (+86)-371-6776-6667 (Y.W.)
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Abstract

The cyclopalladated ferrocenylimine I and its phosphine adducts IIa–f were prepared and evaluated in the borylation of aryl halides. The tricyclohexylphosphine adduct IIb exhibited highly catalytic activity for the coupling of aryl and heteroaryl bromides containing various functional groups with low catalyst loading (2 mol%). Aryl and heteroaryl chlorides were smoothly converted into the corresponding boronates in the presence of the monophosphinobiaryl ligand (XPhos) adduct IIf. It was proposed that palladacycle was only a reservoir of the catalytically active species from the investigation on the reaction mechanism.

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