Hydrotrifluoromethylation and iodotrifluoromethylation of alkenes and alkynes using an inorganic electride as a radical generator

Sungkyu Choi, Ye Ji Kim, Sun Min Kim, Jung Woon Yang (), Sung Wng Kim () and Eun Jin Cho ()
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Sungkyu Choi: Hanyang University
Ye Ji Kim: Sungkyunkwan University
Sun Min Kim: Sungkyunkwan University
Jung Woon Yang: Sungkyunkwan University
Sung Wng Kim: Sungkyunkwan University
Eun Jin Cho: Hanyang University

Nature Communications, 2014, vol. 5, issue 1, 1-7

Abstract: Abstract 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]+·e−, as the electron source. In the transformation, anionic electrons are transferred from [Ca2N]+·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.

Date: 2014
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DOI: 10.1038/ncomms5881

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