Recyclable Copper(I)-Catalyzed Cross-Coupling of Trialkylsilylethynes and N-Tosylhydrazones Leading to the Formation of C(sp)-C(sp³) Bonds

Qian Ye, Wencheng Huang, Li Wei and Mingzhong Cai*

*College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China, Email: mzcaijxnu.edu.cn

Q. Ye, W. Huang, L. Wei, M. Cai, J. Org. Chem., 2023, 88, 2973-2984.

DOI: 10.1021/acs.joc.2c02691

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Abstract

A highly efficient  cross-coupling of trialkylsilylethynes with N-tosylhydrazones has been achieved in dioxane at 90-110 °C using an SBA-15-immobilized l-proline-Cu(I) complex as the heterogeneous catalyst and LiOtBu as the base. The reaction generates a wide variety of alkyltrialkylsilylalkynes in good yields. The recyclable catalyst can be easily recovered through a simple centrifugation.

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proposed mechanism

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Key Words

alkynylation

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ID: J42-Y2023