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

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

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

作者机构:Department of Chemistry Chung-Ang University 84 Heukseok-ro Dong/ak-gu Seou106974 Republic of Korea Department of Applied Chemistry Hanyang University 55 Hanyangdaehak-ro Sangnok-gu Ansan Gyeonggi-do 15588 Republic of Korea 

出 版 物:《Chinese Journal of Chemistry》 (中国化学(英文版))

年 卷 期:2016年第34卷第5期

页      面:459-464页

核心收录:

学科分类:081702[工学-化学工艺] 081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

基  金:supported by the Chung-Ang University Research Scholarship Grants in 2015 National Research Foundation of Korea 

主  题:trifluoroethylation alkyne visible-light photocatalysis 

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.

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