Chemoselective Hydrodehalogenation of Organic Halides Utilizing Two-Dimensional Anionic Electrons of Inorganic Electride [Ca2N]+·e–
详细信息 查看全文
- 作者：Ye Ji Kim ; Sun Min Kim ; Chunghyeon Yu ; YoungMin Yoo ; Eun Jin ChoJung Woon Yang ; Sung Wng Kim
- 刊名：Langmuir
- 出版年：2017
- 出版时间：January 31, 2017
- 年：2017
- 卷：33
- 期：4
- 页码：954-958
- 全文大小：388K
- ISSN：1520-5827
文摘
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.