Synthesis and Structure of Organobismuth Chlorides and Triflates Containing (C,E)-Chelating Ligands (E=O, S) and Their Catalytic Application in the Allylation of Aldehydes with Tetraallyltin

Authors

  • Dr. Nianyuan Tan,

    1. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (P. R. China), Fax: (+86) 731-88821171
    2. College of Chemistry and Chemical Engineering, Hunan Institute of Engineering, Xiangtan 411104 (P. R. China)
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    • These authors contributed equally to this study.

  • Dr. Yi Chen,

    1. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (P. R. China), Fax: (+86) 731-88821171
    2. School of Basic Medicine, Hunan University of Chinese Medicine, Changsha 410208 (P. R. China)
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    • These authors contributed equally to this study.

  • Dr. Yongbo Zhou,

    1. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (P. R. China), Fax: (+86) 731-88821171
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  • Prof. Dr. Chak-Tong Au,

    1. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (P. R. China), Fax: (+86) 731-88821171
    2. Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong (P. R. China)
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  • Prof. Dr. Shuang-Feng Yin

    Corresponding author
    1. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (P. R. China), Fax: (+86) 731-88821171
    • State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (P. R. China), Fax: (+86) 731-88821171

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Abstract

Four air-stable hypervalent organobismuth compounds with (C,O)- or (C,S)-chelating ligands, namely, R2BiCl (R=2-(MeECH2)C6H4; E=O (3), S (4)), [2-(MeOCH2)C6H4]2BiOTf (5), and [{2-(MeSCH2)C6H4}2Bi][OTf] (6; OTf=triflate) were successfully synthesized. The structures of compounds 36 were determined by single-crystal X-ray diffraction. Compound 6 comprises the [2-(MeSCH2)C6H4]2Bi+ cation and the OTf anion. Compounds 5 exhibited good catalytic efficiency and reusability for the allylation reaction of different aldehydes with tetraallyltin in methanol to give the corresponding homoallylic alcohols in excellent yields.

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