4.8 Article

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

Journal

ORGANIC LETTERS
Volume 22, Issue 16, Pages 6600-6604

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c02370

Keywords

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Funding

  1. National Natural Science Foundation of China [21971174, 21772137]
  2. PAPD
  3. Project of Scientific and Technologic Infrastructure of Suzhou [SZS201708]
  4. Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions [16KJA150002]
  5. Postgraduate Research & Practice Innovation Program of Jiangsu Province [KYCX17_1980]
  6. Soochow University
  7. State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials

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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 beta-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.

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