Recent Advances on Annulation Reactions with Allyl and Propargyl Sulfonium Salts

Abstract

Allyl and propargyl sulfonium salts are readily available reagents and have recently emerged as versatile building blocks in the assembly of cyclic skeletons. As an alternative to the classical sulfonium salts, allyl and propargyl sulfonium salts can convert to the corresponding vinyl sulfur ylide or allenic sulfonium salt intermediates that contain diverse nucleophilic or electrophilic reactive positions, thereby enabling a great variety of annulation reactions. In this review, we provide a comprehensive overview of the recent developments on this growing field by summarizing the annulation reactions involving allyl and propargyl sulfonium salts.

Synthetic application of chalcogenonium salts: beyond sulfonium

“…Accordingly, the design, synthesis and application of these salts have been further explored. Alongside their known application as electrophilic 6 or ylide sources, 7 the synthetic use of sulfonium salts can be successfully extended to cross-coupling reactions 8 and the generation of carbon-centered radical species. 9…”

Solvent-involved synthesis of pyrrolidin-5-one-2-carboxamides via a sequential Ugi/olefination reaction

“…1 By taking advantage of a nucleophile and an electrophile, sulfur ylides have been typically utilized as 1,1-dipoles to enable a variety of interesting synthetic transformations. 2 Beyond their application in the classic Corey–Chaykovsky reaction to form cyclopropanes, epoxides, and aziridines, 3 these substances are widely used as key reagents in tandem reactions to furnish five- and six-membered and other fused cyclic compounds (Fig. 1a).…”