4.3 Article

Metal- and additive-free cascade trifluoroethylation/cyclization of organic isoselenocyanates by phenyl(2,2,2-trifluoroethyl)iodonium triflate

Journal

JOURNAL OF FLUORINE CHEMISTRY
Volume 226, Issue -, Pages -

Publisher

ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2019.109360

Keywords

Trifluoroethylation; Cyclization; Isoselenocyanate; Additive-Free; Phenyl(2,2,2-trifluoroethyl)iodonium triflate

Funding

  1. National Natural Science Foundation of China [21602165, 51503037]
  2. Chutian Scholar Program from Department of Education of Hubei Province (China)
  3. Hundred Talent Program of Hubei Province (China)
  4. Chongqing Research Program of Basic and Frontier Technology [cstc2018jcyjAX0106]

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A novel and convenient cascade trifluoroethylation/cyclization of organic isoselenocyanates by phenyl(2,2,2-trifluoroethyl)iodonium triflate is reported. A series of 2-isoselenocyanobiaryls and aryl alkyl isoselenocyanates reacted with phenyl(2,2,2-trifluoroethyl)iodonium triflate in CH2Cl2 at 40 degrees C under metal- and additive-free conditions for 3 h to provide the corresponding trifluoroethylselenolated phenanthridines and 3,4-dihydroisoquinoline derivatives in good to excellent yields. The reaction represents the first general approach to access trifluoroethylselenolated phenanthridines and 3,4-dihydroisoquinolines from organic isoselenocyanates.

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