Nickel-Catalyzed Coupling of N‑Sulfonyl-1,2,3-triazole with H‑Phosphine Oxides: Stereoselective and Site-Selective Synthesis of α‑Aminovinylphosphoryl Derivatives

A nickel-catalyzed coupling of N-sulfonyl-1,2,3-triazole with various H-phosphine oxides for the construction of C­(sp2)–P bonds is established. This unexpected reaction proceeds through a formal nickel-bound ketenimine pathway, representing a previously unknown 1,2-reactivity type of an azavinyl ca...

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Bibliographic Details
Published in:Organic letters 2019-07, Vol.21 (13), p.4944-4949
Main Authors: Liu, Yang, Xie, Peng, Li, Jiagen, Bai, Wen-Ju, Jiang, Jun
Format: Article
Language:English
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Summary:A nickel-catalyzed coupling of N-sulfonyl-1,2,3-triazole with various H-phosphine oxides for the construction of C­(sp2)–P bonds is established. This unexpected reaction proceeds through a formal nickel-bound ketenimine pathway, representing a previously unknown 1,2-reactivity type of an azavinyl carbene. The method provides an efficient approach to the stereoselective and site-selective synthesis of α-aminovinyl­phosphoryl derivatives with moderate to good yield. A plausible mechanism is proposed based on experimental and theoretical studies.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b01288