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
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Funding
- National Natural Science Foundation of China [21602165, 51503037]
- Chutian Scholar Program from Department of Education of Hubei Province (China)
- Hundred Talent Program of Hubei Province (China)
- 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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