Rhodium-Catalyzed [2+2+2] Cycloaddition of Oximes and Diynes To Give Pyridines

Authors

  • Fen Xu,

    1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023 (P. R. China), Fax: (+86) 411-8437-9223
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  • Chunxiang Wang,

    1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023 (P. R. China), Fax: (+86) 411-8437-9223
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  • Dr. Dongping Wang,

    1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023 (P. R. China), Fax: (+86) 411-8437-9223
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  • Dr. Xincheng Li,

    1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023 (P. R. China), Fax: (+86) 411-8437-9223
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  • Prof. Dr. Boshun Wan

    Corresponding author
    1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023 (P. R. China), Fax: (+86) 411-8437-9223
    • Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023 (P. R. China), Fax: (+86) 411-8437-9223
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Abstract

original image

Oximes and diynes undergo efficient cycloaddition in the presence of a catalytic amount of a cationic rhodium(I)/dppf complex (see scheme). Spontaneous dehydration of the initially formed cycloadducts leads to the formation of a variety of substituted pyridines in moderate to good yields. The transformation could also be achieved in a one-pot procedure using aldehydes.

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