Trifluoroethylation of Alkynes： Synthesis of Allylic-CF3 Compounds by Visible-Light Photocatalysis  

作　　者：Geum-bee Roh Naeem Iqbal Eun Jin Cho 

机构地区：[1]Department of Chemistry, Chung-Ang University, 84 Heukseok-ro, Dong/ak-gu, Seou106974, Republic of Korea [2]Department of Applied Chemistry, Hanyang University, 55 Hanyangdaehak-ro, Sangnok-gu, Ansan, Gyeonggi-do 15588, Republic of Korea

出　　处：《Chinese Journal of Chemistry》2016年第5期459-464,共6页中国化学（英文版）

摘　　要：Two types of allylic trifluoromethylated compounds were synthesized by reacting alkynes with CF3CH2I using visible-light photocatalysis. Subtle differences in the catalytic system controlled the selectivity of iodotrifluoroethy- lation and hydrotrifluoroethylation. The iodotrifluoroethylated products were obtained in the presence of [Ru（bpy）3]C12 and TMEDA in CH3CN under visible-light irradiation, whereas hydrotrifluoroethylated products were synthesized usingfac-[Ir（ppy）3] and a mixture of DBU and K2CO3 in DMF. The iodotrifluoroethylation reac- tion worked particularly well, even at gram-scale, and the synthetic utility of iodotrifluoroethylated products was proved by their coupling reactions, providing complex CF3-containing products.Two types of allylic trifluoromethylated compounds were synthesized by reacting alkynes with CF3CH2I using visible-light photocatalysis. Subtle differences in the catalytic system controlled the selectivity of iodotrifluoroethy- lation and hydrotrifluoroethylation. The iodotrifluoroethylated products were obtained in the presence of [Ru（bpy）3]C12 and TMEDA in CH3CN under visible-light irradiation, whereas hydrotrifluoroethylated products were synthesized usingfac-[Ir（ppy）3] and a mixture of DBU and K2CO3 in DMF. The iodotrifluoroethylation reac- tion worked particularly well, even at gram-scale, and the synthetic utility of iodotrifluoroethylated products was proved by their coupling reactions, providing complex CF3-containing products.

关 键 词：TRIFLUOROETHYLATION ALKYNE VISIBLE-LIGHT PHOTOCATALYSIS 

分 类 号：TQ637.3[化学工程—精细化工] O623.612[理学—有机化学]