Insights into the multifaceted applications of vinyl sulfoxonium ylides

Abstract

Sulfoxonium ylides are important synthetic precursors in various organic transformations. Their synthetic potential was well explored in the synthesis of various bioactive natural products and pharmaceuticals. Vinyl sulfoxonium ylide is...

Stereoselective gem-Difunctionalization of Diazo Compounds with Vinyl Sulfoxonium Ylides and Thiols via Metalloradical Catalysis

“…Between these two carbene precursors, diazo compounds react faster under metal-catalyzed conditions than sulfoxonium ylides and generate a reactive electrophilic carbene intermediate, which is then trapped by sulfoxonium ylide as a nucleophile. Prompted by this observation and our continuing interest in sulfoxonium ylides, − we were intrigued to obtain stereoselective gem -difunctionalization of diazo compounds with the thiols and sulfoxonium ylides to obtain tertiary sulfide compounds, which are basic scaffolds for various natural products and medicinally important compounds. , …”

Visible Light-Promoted Regioselective Benzannulation of Vinyl Sulfoxonium Ylides with Ynoates

“…The major challenges associated with the light-mediated conversion of sulfoxonium ylides are the light absorption of ylides as well as the leaving ability of DMSO (Scheme b) . As part of our ongoing research interest in sulfur ylides − and intrigued by metal-free carbene generation from diazo compounds, we would like to explore the reactivity of vinyl sulfoxonium ylide in the presence of blue light to open up a new avenue of sulfoxonium ylide based photochemistry. − …”

Diastereoselective cyclopropanation of α,β-unsaturated carbonyl compounds with vinyl sulfoxonium ylides

“…5 Vinyl sulfoxonium ylides can undergo electrophilic addition at the αor γ-carbon due to their dipole structure (Scheme 1b). 6 Recently, our group developed a method to synthesize 2H-chromenes via catalyst-controlled regioselective [3 + 3] annulation of vinyl sulfoxonium ylides with quinones. In the absence of a metal catalyst, vinyl sulfoxonium ylide reacts with the quinone at the γ-position of the ylide, followed by cyclization to give 2H-chromene-4-carboxylate.…”