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Synthesis of Terminal Allenes through Copper-Mediated Cross-Coupling of Ethyne with N-Tosylhydrazones or α-Diazoesters

Fei Ye, Chengpeng Wang, Xiaoshen Ma, Mohammad Lokman Hossain, Ying Xia, Yan Zhang and Jianbo Wang*

*Beijing National Laboratory of Molecular Sciences (BNLMS), College of Chemistry, Peking University, Beijing 100871, China, Email:

F. Ye, C. Wang, X. Ma, M. L. Hossain, Y. Xia, Y. Zhang, J. Wang, J. Org. Chem., 2015, 80, 647-652.

DOI: 10.1021/jo502316q

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Terminal allenes can be synthesized in good yields using ethyne as coupling partner in a copper-mediated cross-coupling reaction with N-tosylhydrazones or α-diazoacetate. This coupling method offers excellent functional group tolerance. Copper carbene migratory insertion is proposed as the key step.

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CuI-Catalyzed Cross-Coupling of N-Tosylhydrazones with Terminal Alkynes: Synthesis of 1,3-Disubstituted Allenes

M. L. Hossain, F. Ye, Y. Zhang, J. Wang, J. Org. Chem., 2013, 78, 1236-1241.

Key Words


ID: J42-Y2015