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Computational Investigations on the Transition-Metal-Catalyzed Cross-Coupling of Enynones with Diazo Compounds

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Abstract

Computational studies were carried out to understand the mechanisms of Au(I)- and Zn(II)-catalyzed cross-coupling of enynones with diazo compounds to produce multisubstituted furylalkenes. Although both enynones and diazo compounds can be converted to the corresponding metal-carbene intermediates, it is more ready for the enynones to undergo intramolecular nucleophilic cyclization to afford a 2-furyl metal-carbene intermediate for both Au(I)- and Zn(II)-catalysis. For the di-gold catalyzed cross-coupling of enynones with diazo compounds, the sequential activation of enynones and diazo compounds could result in a di-gold carbenoid species, which could undergo a reductive elimination step to produce the final multisubstituted furylalkenes. While, after the formation the 2-furyl Zn(II)-carbene intermediate, the nucleophilic C-attack of diazo compound to the carbene moiety could proceed to result in the desired product. The origin of stereoselectivity in the multisubstituted furylalkenes is discussed.

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Acknowledgements

We are grateful to the National Natural Science Foundation of China (21973068) for financial support.

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Authors and Affiliations

  1. Innovation Center for Chemical Sciences, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, Jiangsu, China

    Tiantian Liu, Kang Lv & Xiaoguang Bao

  2. Department of Chemistry and Chemical Engineering, Jining University, Qufu, 273155, Shandong, China

    Kang Lv

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  1. Tiantian Liu
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Correspondence to Xiaoguang Bao.

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Liu, T., Lv, K. & Bao, X. Computational Investigations on the Transition-Metal-Catalyzed Cross-Coupling of Enynones with Diazo Compounds. Top Catal 65, 462–471 (2022). https://doi.org/10.1007/s11244-021-01484-3

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