Chemoselective hydrodehalogenation of organic halides utilizing two-dimensional anionic electrons of inorganic electride [Ca2N]+·e
- 관리정보기술 faculty
- 등재 SCIE, SCOPUS
- 발행기관 American Chemical Society
- 발행년도 2017
- URI http://www.dcollection.net/handler/ewha/000000141756
- 본문언어 영어
- Published As http://dx.doi.org/10.1021/acs.langmuir.6b04152
- 저작권 이화여자대학교 논문은 저작권에 의해 보호받습니다.
초록/요약
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). © 2017 American Chemical Society.
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