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Controllable Mono-/Dialkenylation of Benzyl Thioethers through Rh-Catalyzed Aryl C[BOND]H Activation

Authors

  • Xi-Sha Zhang,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering and Green Chemistry Center, Peking University, Beijing 100871 (P.R. China)
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  • Qi-Lei Zhu,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering and Green Chemistry Center, Peking University, Beijing 100871 (P.R. China)
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  • Yun-Fei Zhang,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering and Green Chemistry Center, Peking University, Beijing 100871 (P.R. China)
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  • Yan-Bang Li,

    1. Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering and Green Chemistry Center, Peking University, Beijing 100871 (P.R. China)
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  • Prof. Dr. Zhang-Jie Shi

    Corresponding author
    1. Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering and Green Chemistry Center, Peking University, Beijing 100871 (P.R. China)
    2. State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032 (P.R. China)
    • Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering and Green Chemistry Center, Peking University, Beijing 100871 (P.R. China)
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Abstract

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Under solvent control: Benzyl thioethers were alkenylated in excellent yields with broad substrate scope and the selectivity (mono- vs. disubstituted product) was controlled by the solvent and ratio of reactants (see scheme). Sequential alkenylation with two different alkenes was also carried out in a one-pot process. In addition, the thioether directing group was removed in a one-pot process with simultaneous hydrogenation of the double bond to give the toluene derivatives.

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