(3+2) Cycloadditions of Vinyl Sulfonyl Fluorides with Ethyl Diazoacetate or Azides: Metal-Free Synthesis of Pyrazole and Triazole Scaffolds via SO₂ Elimination

Abstract

A (3+2) cycloaddition reaction between substituted vinyl sulfonyl fluorides and ethyl diazoacetate or azides for the rapid construction of pyrazole or triazole cores via Michael addition and SO₂ gas elimination is developed. Trimethylsilyl azide or organic azide selectively attacks at the β-carbon of vinyl sulfonyl fluoride rather than at the S(VI) center and generates C-substituted or C,N-disubstituted triazole. In contrast, vinyl sulfonyl fluorides react with ethyl diazoacetate to generate pyrazoles in good to high yields.

Key words

azides - cycloaddition - diazo compounds - Michael addition - pyrazole - triazole - vinyl sulfonyl fluoride

Publication History

Received: 26 March 2022

Accepted: 19 April 2022

Article published online:
09 June 2022

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