title: Hydrotrifluoromethylation and iodotrifluoromethylation of alkenes and alkynes using an inorganic electride as a radical generator.
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.
authors.affiliation: Department of Bionanotechnology, Hanyang University, 55 Hanyangdaehak-ro, Sangnok-gu, Ansan 426-791, Republic of Korea.
authors.forename: Sungkyu
authors.initials: S
authors.lastname: Choi
authors.affiliation: 1] Department of Energy Science, Sungkyunkwan University, Suwon 440-746, Republic of Korea [2] IBS Centre for Integrated Nanostructure Physics, Institute for Basic Science, Daejeon 305-791, Republic of Korea.
authors.forename: Ye Ji
authors.initials: YJ
authors.lastname: Kim
authors.affiliation: Department of Energy Science, Sungkyunkwan University, Suwon 440-746, Republic of Korea.
authors.forename: Sun Min
authors.initials: SM
authors.lastname: Kim
authors.affiliation: Department of Energy Science, Sungkyunkwan University, Suwon 440-746, Republic of Korea.
authors.forename: Jung Woon
authors.initials: JW
authors.lastname: Yang
authors.affiliation: 1] Department of Energy Science, Sungkyunkwan University, Suwon 440-746, Republic of Korea [2] IBS Centre for Integrated Nanostructure Physics, Institute for Basic Science, Daejeon 305-791, Republic of Korea.
authors.forename: Sung Wng
authors.initials: SW
authors.lastname: Kim
authors.affiliation: 1] Department of Bionanotechnology, Hanyang University, 55 Hanyangdaehak-ro, Sangnok-gu, Ansan 426-791, Republic of Korea [2] Center for New Directions in Organic Synthesis, Department of Chemistry and Applied Chemistry, Hanyang University, Ansan 426-791, Republic of Korea.
authors.forename: Eun Jin
authors.initials: EJ
authors.lastname: Cho