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나노 구조 물리 연구단
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Hydrotrifluoromethylation and iodotrifluoromethylation of alkenes and alkynes using an inorganic electride as a radical generator

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Title
Hydrotrifluoromethylation and iodotrifluoromethylation of alkenes and alkynes using an inorganic electride as a radical generator
Author(s)
Sungkyu Choi; Ye Ji Kim; Sun Min Kim; Jung Woon Yang; Sung Wng Kim; Eun Jin Cho
Publication Date
2014-09
Journal
NATURE COMMUNICATIONS, v.5, no., pp.4881 -
Publisher
NATURE PUBLISHING GROUP
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]þ e, as the electron source. In the transformation, anionic electrons are transferred from [Ca2N]þ 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.
URI
http://pr.ibs.re.kr/handle/8788114/781
DOI
10.1038/ncomms5881
ISSN
2041-1723
Appears in Collections:
Center for Integrated Nanostructure Physics(나노구조물리 연구단) > Journal Papers (저널논문)
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