Chemoselective hydrodehalogenation of organic halides utilizing two-dimensional anionic electrons of inorganic electride [Ca2N]+·e-

Ye Ji Kim, Sun Min Kim, Chunghyeon Yu, Youngmin Yoo, Eun Jin Cho, Jung Woon Yang, Sung Wng Kim

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

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. (Chemical Equation Presented).

Original languageEnglish
Pages (from-to)954-958
Number of pages5
JournalLangmuir
Volume33
Issue number4
DOIs
StatePublished - 31 Jan 2017

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