期刊
NATURE COMMUNICATIONS
卷 5, 期 -, 页码 -出版社
NATURE PUBLISHING GROUP
DOI: 10.1038/ncomms5881
关键词
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资金
- National Research Foundation of Korea (NRF) [NRF-2014R1A1A1A05003274, NRF-2014-011165, NRF-2012M3A7B4049657, NRF 2013R1A1A1008025]
- JSPS FIRST
- JST ACCEL Program
The trifluoromethyl (CF3) group is a staple synthon that can alter the physical and chemical properties of organic molecules. Despite recent advances in trifluoromethylation methods, the development of a general synthetic methodology for efficient and selective trifluoromethylation remains an ongoing challenge motivated by a steadily increasing demand from the pharmaceutical, agrochemical and materials science industries. In this article, we describe a simple, efficient and environmentally benign strategy for the hydrotrifluoromethylation of unactivated alkenes and alkynes through a radical-mediated reaction using an inorganic electride, [Ca2N](+)center dot e(-), as the electron source. In the transformation, anionic electrons are transferred from [Ca2N](+)center dot e(-) electrides to the trifluoromethylating reagent CF3I to initiate radical-mediated trifluoromethylation. The role of ethanol is pivotal in the transformation, acting as the solvent, an electron-releasing promoter and a hydrogen atom source. In addition, iodotrifluoromethylation of alkynes proceeds selectively upon the control of electride amount.
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