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Birch Reduction of Aromatic Compounds by Inorganic Electride [Ca2N](+center dot)e(-) in an Alcoholic Solvent: An Analogue of Solvated Electrons

Title
Birch Reduction of Aromatic Compounds by Inorganic Electride [Ca2N](+center dot)e(-) in an Alcoholic Solvent: An Analogue of Solvated Electrons
Authors
Il Yoo, ByungKim, Ye JiYou, YoungMinYang, Jung WoonKim, Sung Wng
Ewha Authors
유영민
SCOPUS Author ID
유영민scopus
Issue Date
2018
Journal Title
JOURNAL OF ORGANIC CHEMISTRY
ISSN
0022-3263JCR Link
Citation
JOURNAL OF ORGANIC CHEMISTRY vol. 83, no. 22, pp. 13847 - 13853
Publisher
AMER CHEMICAL SOC
Indexed
SCI; SCIE; SCOPUS WOS
Document Type
Article
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.
DOI
10.1021/acs.joc.8b02094
Appears in Collections:
엘텍공과대학 > 화학신소재공학전공 > Journal papers
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