Birch Reduction of Aromatic Compounds by Inorganic Electride [Ca2N](+center dot)e(-) in an Alcoholic Solvent: An Analogue of Solvated Electrons
- 주제(기타) Chemistry, Organic
- 설명문(일반) [Il Yoo, Byung; Kim, Ye Ji; Yang, Jung Woon; Kim, Sung Wng] Sungkyunkwan Univ, Dept Energy Sci, Suwon 440746, South Korea; [Kim, Ye Ji] Sungkyunkwan Univ, IBS, Ctr Integrated Nanostruct Phys, Suwon 440746, South Korea; [You, YoungMin] Ewha Womans Univ, Div Chem Engn & Mat Sci, Seoul 120750, South Korea
- 관리정보기술 faculty
- 등재 SCIE, SCOPUS
- 발행기관 AMER CHEMICAL SOC
- 발행년도 2018
- URI http://www.dcollection.net/handler/ewha/000000156358
- 본문언어 영어
- Published As http://dx.doi.org/10.1021/acs.joc.8b02094
초록/요약
Birch reduction of aromatic systems by solvated electrons in alkali metal-ammonia solutions is widely recognized as a key reaction that functionalizes highly stable pi-conjugated organic systems. In spite of recent advances in Birch reduction with regard to reducing agent and reaction conditions, there remains an ongoing challenge to develop a simple and efficient Birch reaction under mild conditions. Here, we demonstrate that the inorganic electride [Ca2N](+center dot)e(-) promotes the Birch reduction of polycyclic aromatic hydrocarbons (PAHs) and naphthalene under alcoholic solvent in the vicinity of room temperature as a solid-type analogy to solvated electrons in alkali metal ammonia solutions. The anionic electrons from electride [Ca2N](+center dot)e(-) are transferred to PAHs and naphthalene via alcoholysis in a polar cosolvent medium. It is noteworthy that a high conversion yield to the hydrogenated products is ascribed to the extremely high electron transfer efficiency of 98%. This simple protocol utilizing an inorganic electride offers a direct and practical strategy for the reduction of aromatic compounds and provides an outstanding reducing agent for synthetic chemistry.
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