title: Chemoselective Hydrodehalogenation of Organic Halides Utilizing Two-Dimensional Anionic Electrons of Inorganic Electride [Ca2N]+·e<sup/>.
abstract: Halogenated organic compounds are important anthropogenic chemicals widely used in chemical industry, biology, and pharmacology; however, the persistence and inertness of organic halides cause human health problems and considerable environmental pollution. Thus, the elimination or replacement of halogen atoms with organic halides has been considered a central task in synthetic chemistry. In dehalogenation reactions, the consecutive single-electron transfer from reducing agents generates the radical and corresponding carbanion and thus removes the halogen atom as the leaving group. Herein, we report a new strategy for an efficient chemoselective hydrodehalogenation through the formation of stable carbanion intermediates, which are simply achieved by using highly mobile two-dimensional electrons of inorganic electride [Ca2N]+·e-with effective electron transfer ability. The consecutive single-electron transfer from inorganic electride [Ca2N]+·e-stabilized free carbanions, which is a key step in achieving the selective reaction. Furthermore, a determinant more important than leaving group ability is the stability control of free carbanions according to the s character determined by the backbone structure. We anticipate that this approach may provide new insight into selective chemical formation, including hydrodehalogenation.
authors.affiliation: Department of Energy Science, Sungkyunkwan University , Suwon 440-746, Republic of Korea.
authors.forename: Ye Ji
authors.initials: YJ
authors.lastname: Kim
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Sun Min
authors.initials: SM
authors.lastname: Kim
authors.affiliation: Department of Bionanotechnology, Hanyang University , Ansan, Kyeonggi-do 426-791, Republic of Korea.
authors.forename: Chunghyeon
authors.initials: C
authors.lastname: Yu
authors.affiliation: Division of Chemical Engineering and Materials Science, Ewha Womans University , Seoul 120-750, Republic of Korea.
authors.forename: YoungMin
authors.initials: Y
authors.lastname: Yoo
authors.affiliation: Department of Chemistry, Chung-Ang University , Seoul 156-756, Republic of Korea.
authors.forename: Eun Jin
authors.identifier: 0000-0002-6607-1851
authors.initials: EJ
authors.lastname: Cho
authors.affiliation: Department of Energy Science, Sungkyunkwan University , Suwon 440-746, Republic of Korea.
authors.forename: Jung Woon
authors.identifier: 0000-0001-8636-0901
authors.initials: JW
authors.lastname: Yang
authors.affiliation: Department of Energy Science, Sungkyunkwan University , Suwon 440-746, Republic of Korea.
authors.forename: Sung Wng
authors.identifier: 0000-0002-4802-5421
authors.initials: SW
authors.lastname: Kim