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Silver-Mediated [3 + 2] Cycloaddition of Alkynes and N-Isocyanoiminotriphenylphosphorane: Access to Monosubstituted Pyrazoles

Fanhua Yi, Wanjun Zhao, Zikun Wang*, Xihe Bi*

*Department of Chemistry, Northeast Normal University, Changchun 130024, China, Email:,

F. Yi, W. Zhao, Z. Wang, X. Bi, Org. Lett., 2019, 21, 3158-3161.

DOI: 10.1021/acs.orglett.9b00860

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A silver-mediated [3 + 2] cycloaddition of N-isocyanoiminotriphenylphosphorane as "CNN" building block to terminal alkynes provides pyrazoles. N-isocyanoiminotriphenylphosphorane is a stable, safe, easy-to-handle, and odorless solid isocyanide. The reaction offers mild conditions, broad substrate scope, and excellent functional group tolerance.

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proposed mechanism

Key Words


ID: J54-Y2019