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Fe-Catalyzed Fluorosulfonylation of Alkenes via Sulfur Dioxide Insertion: Synthesis of Lactam-Functionalized Alkyl Sulfonyl Fluorides.
Sun, Da-Zhi; Hu, Xiaojun; Long, Fang; Peng, Chuan-Chong; Zhang, Kai-Yi; Li, Qing; Liu, Jin-Hui; Wu, Li-Jun; Yin, Shuang-Feng.
Afiliação
  • Sun DZ; College of Chemistry and Chemical Engineering, Central South University of Forestry and Technology, Changsha 410004, China.
  • Hu X; Hunan Provincial Institute of Product and Goods Quality Inspection, Changsha 410007, China.
  • Long F; College of Chemistry and Chemical Engineering, Central South University of Forestry and Technology, Changsha 410004, China.
  • Peng CC; Department of Hunan Cuisine, ChangSha Commerce & Tourism College, Changsha 410116, China.
  • Zhang KY; College of Chemistry and Chemical Engineering, Central South University of Forestry and Technology, Changsha 410004, China.
  • Li Q; College of Chemistry and Chemical Engineering, Central South University of Forestry and Technology, Changsha 410004, China.
  • Liu JH; College of Chemistry and Chemical Engineering, Central South University of Forestry and Technology, Changsha 410004, China.
  • Wu LJ; College of Chemistry and Chemical Engineering, Central South University of Forestry and Technology, Changsha 410004, China.
  • Yin SF; College of Chemistry and Chemical Engineering, Central South University of Forestry and Technology, Changsha 410004, China.
Org Lett ; 26(33): 6983-6987, 2024 Aug 23.
Article em En | MEDLINE | ID: mdl-39140705
ABSTRACT
A novel Fe-catalyzed fluorosulfonylation of alkenes with Na2S2O4 and N-fluorobenzenesulfonimide (NFSI) for assembling various lactam-functionalized alkyl sulfonyl fluorides is disclosed. In this reaction, Na2S2O4 acts as both an SO2 source and a reductant. Furthermore, the resulting products can be efficiently transformed into valuable chemicals, including sulfonyl esters and sulfonamides, via the sulfur(VI) fluoride exchange (SuFEx) click reaction. Preliminary mechanistic studies suggest that the transformation proceeds through intramolecular radical cyclization, SO2 insertion, sulfite anion formation, and fluorination.

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Org Lett Assunto da revista: BIOQUIMICA Ano de publicação: 2024 Tipo de documento: Article País de afiliação: China País de publicação: Estados Unidos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Org Lett Assunto da revista: BIOQUIMICA Ano de publicação: 2024 Tipo de documento: Article País de afiliação: China País de publicação: Estados Unidos