Birch Reduction of Aromatic Compounds by Inorganic Electride [Ca2N]+•e– in an Alcoholic Solvent: An Analogue of Solvated Electrons

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Title
Birch Reduction of Aromatic Compounds by Inorganic Electride [Ca2N]+•e– in an Alcoholic Solvent: An Analogue of Solvated Electrons
Author(s)
Byung Il Yoo; Ye Ji Kim; YoungMin You; Yang Jung Woon; Sung Wng Kim
Publication Date
2018-11
Journal
JOURNAL OF ORGANIC CHEMISTRY, v.83, no.22, pp.13847 - 13853
Publisher
AMER CHEMICAL SOC
Abstract
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 © 2018 American Chemical Society
URI
https://pr.ibs.re.kr/handle/8788114/5408
ISSN
0022-3263
Appears in Collections:
Center for Integrated Nanostructure Physics(나노구조물리 연구단) > Journal Papers (저널논문)
Files in This Item:
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