Metal-Free Chemoselective Reaction of Sulfoxonium Ylides and Thiosulfonates: Diverse Synthesis of 1,4-Diketones, Aryl Sulfursulfoxonium Ylides, and β-Keto Thiosulfones Derivatives

Fei Wang; Bo-Xi Liu; Weidong Rao; Shun-Yi Wang

doi:10.1021/acs.orglett.0c02370

Metal-Free Chemoselective Reaction of Sulfoxonium Ylides and Thiosulfonates: Diverse Synthesis of 1,4-Diketones, Aryl Sulfursulfoxonium Ylides, and β-Keto Thiosulfones Derivatives

Org Lett. 2020 Aug 21;22(16):6600-6604. doi: 10.1021/acs.orglett.0c02370. Epub 2020 Aug 10.

Authors

Fei Wang¹, Bo-Xi Liu¹, Weidong Rao², Shun-Yi Wang¹

Affiliations

¹ Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou, 215123, China.
² Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, College and Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China.

PMID: 32806158
DOI: 10.1021/acs.orglett.0c02370

Abstract

A diverse chemoselective insertion reaction of sulfoxonium ylides and thiosulfonates under transition-metal-free conditions is developed, which successfully affords 1,4-diketone compounds, arylthiosulfoxide-ylides, and β-keto thiosulfones, respectively. The nucleophilic addition of two molecular sulfoxonium ylides to construct sulfone-substituted 1,4-dione compounds is the highlight of this work.