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Trifluoroethylation of Alkynes: Synthesis of Allylic-CF3 Compounds by Visible-Light Photocatalysis
- Authors
- Roh, Geum-bee; Iqbal, Naeem; Cho, Eun Jin
- Issue Date
- May-2016
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- trifluoroethylation; alkyne; visible-light; photocatalysis
- Citation
- CHINESE JOURNAL OF CHEMISTRY, v.34, no.5, pp 459 - 464
- Pages
- 6
- Journal Title
- CHINESE JOURNAL OF CHEMISTRY
- Volume
- 34
- Number
- 5
- Start Page
- 459
- End Page
- 464
- ISSN
- 1001-604X
1614-7065
- Abstract
- 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 iodotrifluoroethylation and hydrotrifluoroethylation. The iodotrifluoroethylated products were obtained in the presence of [Ru(bpy)(3)]Cl-2 and TMEDA in CH3CN under visible-light irradiation, whereas hydrotrifluoroethylated products were synthesized using fac-[Ir(ppy)(3)] and a mixture of DBU and K2CO3 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 CF3-containing products.
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