Vinyl Sulfoxonium Ylide: A New Vinyl Carbenoid Transfer Reagent for the Synthesis of Heterocycles

Abstract

Sulfoxonium ylides have recently gained prominence as safe carbenoid precursors in metal-catalyzed reactions. The stability and reactivity of sulfoxonium ylides depend on the substitution of the ylide carbon. The reactivity of vinyl-substituted sulfoxonium ylides is different and offers several advantages over known stabilized sulfoxonium ylides in the case of carbenoid transfer reactions. Herein, we provide an overview of early efforts in this area, with particular emphasis on our own recent development of sulfoxonium ylide-derived vinyl carbenoid transformations for N-Heterocycles.

1 Introduction

2 Classification of Sulfoxonium Ylides

3 Synthesis of Vinyl Sulfoxonium Ylides

4 [3+2] Annulation of Vinyl Sulfoxonium Ylides

5 [4+1] Annulation of Vinyl Sulfoxonium Ylides

6 Conclusion

Key words

sulfoxonium ylides - metal carbenoids - transition-metal catalysis - insertion reactions - heterocycles

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