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Trifluoroethylation of Alkynes: Synthesis of Allylic‐CF 3 Compounds by Visible‐Light Photocatalysis
Author(s) -
Roh Geumbee,
Iqbal Naeem,
Cho Eun Jin
Publication year - 2016
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201500919
Subject(s) - chemistry , photocatalysis , allylic rearrangement , visible spectrum , catalysis , selectivity , photochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , optoelectronics , physics
Two types of allylic trifluoromethylated compounds were synthesized by reacting alkynes with CF 3 CH 2 I using visible‐light photocatalysis. Subtle differences in the catalytic system controlled the selectivity of iodotrifluoroethylation and hydrotrifluoroethylation. The iodotrifluoroethylated products were obtained in the presence of [Ru(bpy) 3 ]Cl 2 and TMEDA in CH 3 CN under visible‐light irradiation, whereas hydrotrifluoroethylated products were synthesized using fac ‐[Ir(ppy) 3 ] and a mixture of DBU and K 2 CO 3 in DMF. The iodotrifluoroethylation reaction worked particularly well, even at gram‐scale, and the synthetic utility of iodotrifluoroethylated products was proved by their coupling reactions, providing complex CF 3 ‐containing products.