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

Janakiram Vaitla; Annette Bayer; Kathrin H. Hopmann

doi:10.1055/s-0037-1611771

Synlett, Table of Contents

Synlett 2019; 30(12): 1377-1383
DOI: 10.1055/s-0037-1611771

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

Janakiram Vaitla *

^aHylleraas Centre for Quantum Molecular Sciences, Department of Chemistry, University of Tromsø – The Arctic University of Norway, 9037 Tromsø, Norway

^bDepartment of Chemistry, University of Tromsø – The Arctic University of Norway, 9037 Tromsø, Norway Email: janakiray.vaitla@uit.no Email: kathrin.hopmann@uit.no

,

Annette Bayer

^bDepartment of Chemistry, University of Tromsø – The Arctic University of Norway, 9037 Tromsø, Norway Email: janakiray.vaitla@uit.no Email: kathrin.hopmann@uit.no

,

Kathrin H. Hopmann*

^aHylleraas Centre for Quantum Molecular Sciences, Department of Chemistry, University of Tromsø – The Arctic University of Norway, 9037 Tromsø, Norway

^bDepartment of Chemistry, University of Tromsø – The Arctic University of Norway, 9037 Tromsø, Norway Email: janakiray.vaitla@uit.no Email: kathrin.hopmann@uit.no

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Abstract

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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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References

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