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[3 + 2] Cycloaddition Reaction of Vinylsulfonium Salts with Hydrazonoyl Halides: Synthesis of Pyrazoles

Wen-Jing Luo, Xiuwen Liang, Maizhuo Chen, Ke‐Hu Wang, Danfeng Huang, Junjiao Wang, Dongping Chen, Yulai Hu

2024The Journal of Organic Chemistry18 citationsDOI

Abstract

generated nitrile imines from hydrazonoyl halides and vinylsulfonium salts is developed. The nitrile imines are demonstrated to be a new class of reaction partner for vinylsulfonium salts to conduct the [3 + 2] cycloaddition reaction. The process provides a concise and efficient method for the construction of pyrazole derivatives under mild reaction conditions with broad substrate scope, good product yields, and high regioselectivity.

Topics & Concepts

ChemistryCycloadditionHalideCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalysisFluorine in Organic ChemistryCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions
[3 + 2] Cycloaddition Reaction of Vinylsulfonium Salts with Hydrazonoyl Halides: Synthesis of Pyrazoles | Litcius