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Rhodium(III)-catalyzed [3+2] annulative coupling between oximes and electron-deficient alkynes

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Abstract

Rhodium(III)-catalyzed coupling between ketoximes and alkynes via C-H activation and annulation typically followed the [4+2] selectivity to afford isoquinolines. By designing alkynes bearing a highly electron-withdrawing group and under substrate control, we have successfully switched the selectivity of the coupling between oximes and alkynes to the alternative [3+2] annulation, leading to the efficient synthesis of indenamines. This process features good regioselectivity for both substrates, high efficiency, broad substrate scope, and excellent functional group tolerance.

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Authors and Affiliations

  1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China

    Xukai Zhou, Songjie Yu, Zisong Qi & Xingwei Li

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  1. Xukai Zhou
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  2. Songjie Yu
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  4. Xingwei Li
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Correspondence to Xingwei Li.

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Zhou, X., Yu, S., Qi, Z. et al. Rhodium(III)-catalyzed [3+2] annulative coupling between oximes and electron-deficient alkynes. Sci. China Chem. 58, 1297–1301 (2015). https://doi.org/10.1007/s11426-015-5408-8

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  • DOI: https://doi.org/10.1007/s11426-015-5408-8

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