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Photocatalytic Remote Oxyfluoroalkylation of Heteroalkynes: Regio-, Stereo-, and Site-Selective Access to Complex Fluoroalkylated (Z)-Alkenes.
Shang, Tianbo; Zhang, Junhua; Zhang, Yan; Zhang, Fang; Li, Xin-Sheng; Zhu, Gangguo.
Affiliation
  • Shang T; Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, P. R. China.
  • Zhang J; Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, P. R. China.
  • Zhang Y; Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, P. R. China.
  • Zhang F; Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, P. R. China.
  • Li XS; Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, P. R. China.
  • Zhu G; Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, P. R. China.
Org Lett ; 22(9): 3667-3672, 2020 May 01.
Article in En | MEDLINE | ID: mdl-32275159
ABSTRACT
A visible-light-induced remote oxyfluoroalkylation, including ketofluoroalkylation and hydroxytrifluoromethylation, of heteroalkynes is developed with dimethyl sulfoxide (DMSO) and H2O as the oxygen source, respectively. It provides a facile access to complex fluoroalkylated (Z)-alkenes in satisfactory yields with excellent regio-, stereo-, and site-selectivity. The reaction involves an uncommon vinyl radical-induced intermolecular C(sp3)-H functionalization, thus offering a good platform for the development of remote difunctionalization of alkynes.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2020 Document type: Article
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2020 Document type: Article