4.5 Article

(Trifluoromethyl)thiolation of 2-Alkynylbenzoates: An Efficient Route to 4-[(Trifluoromethyl)thio]-1H-isochromen-1-ones

期刊

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2014, 期 23, 页码 5017-5022

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201402629

关键词

Fluorine; Sulfur; Cyclization; Alkynes; Oxygen heterocycles; Lewis acid catalysis

资金

  1. National Natural Science Foundation of China [21262016]
  2. Project of Jiangxi Youth Scientist [20122BCB23012]
  3. Jiangxi Educational Committee [GJJ12169]
  4. Visiting Programme of Jiangxi Normal University graduate
  5. Natural Science Foundation of Jiangxi Province of China [20133ACB20008, 20132BAB203006]

向作者/读者索取更多资源

The incorporation of the (trifluoromethyl)thio group into the isocoumarin scaffold through a Lewis-acid-mediated electrophilic cyclization reaction of 2-(2-alkynyl)benzoates with trifluoromethanesulfanylamide is reported. The transformation proceeds well in the presence of BiCl3 and BF3 center dot Et2O under mild conditions to give 4-[(trifluoromethyl)thio]-1H-isochromen-1-ones regioselectively and in good yields.

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