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Cross Dehydrogenative Arylation (CDA) of a Benzylic C[BOND]H Bond with Arenes by Iron Catalysis

Authors

  • Yi-Zhou Li,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS), PKU Green Chemistry Centre and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871 (China), Fax: (+86) 10-6276-0890, http://www.shigroup.cn/
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    • These authors contributed equally to this research.

  • Bi-Jie Li,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS), PKU Green Chemistry Centre and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871 (China), Fax: (+86) 10-6276-0890, http://www.shigroup.cn/
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    • These authors contributed equally to this research.

  • Xing-Yu Lu,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS), PKU Green Chemistry Centre and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871 (China), Fax: (+86) 10-6276-0890, http://www.shigroup.cn/
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  • Song Lin,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS), PKU Green Chemistry Centre and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871 (China), Fax: (+86) 10-6276-0890, http://www.shigroup.cn/
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  • Zhang-Jie Shi Prof. Dr.

    1. Beijing National Laboratory of Molecular Sciences (BNLMS), PKU Green Chemistry Centre and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871 (China), Fax: (+86) 10-6276-0890, http://www.shigroup.cn/
    2. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032 (China)
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  • This work was supported by a starter grant from Peking University, grants from the National Sciences of Foundation of China (nos. 20672006, 20821062, GZ419, J0630421) , and the “973” Project from the MOST of China (2009CB825300).

Abstract

Hooking up: FeCl2 catalyzes the efficient cross dehydrogenative arylation of substrates having benzylic C[BOND]H bonds (see scheme). High regioselectivity was observed during the cross-coupling between compounds containing aromatic C(sp2)[BOND]H bonds and benzylic C(sp3)[BOND]H bonds. This process is proposed to proceed by single-electron-transfer oxidation and Friedel–Crafts alkylation.

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