Base-induced dehydrogenative and dearomative transformation of 1-naphthylmethylamines to 1,4-dihydronaphthalene-1-carbonitriles

Base-induced dehydrogenative and dearomative transformation of 1-naphthylmethylamines to 1,4-dihydronaphthalene-1-carbonitriles

Solvothermal treatment of 1-naphthylmethylamine with potassium hydride (KH) or n-butyllithium (n-BuLi)-potassium t-butoxide (t-BuOK) in THF induces unusual two consecutive β-hydride eliminations to form 1-naphthonitrile and KH. The freshly generated KH is hydridic enough to undergo dearomative hydri...

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Bibliographic Details
Main Authors: Sekiguchi, Yoshiya, Pang, Jia Hao, Ng, Jia Sheng, Chen, Jiahua, Watanabe, Kohei, Takita, Ryo, Chiba, Shunsuke
Other Authors: School of Chemistry, Chemical Engineering and Biotechnology
Format: Article
Language:English
Published: 2023
Subjects:
Engineering::Chemical engineering
Dearomatization
Beta-Hydride Elimination
Online Access:https://hdl.handle.net/10356/164489
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Institution: Nanyang Technological University
Language: English
Description
Summary:Solvothermal treatment of 1-naphthylmethylamine with potassium hydride (KH) or n-butyllithium (n-BuLi)-potassium t-butoxide (t-BuOK) in THF induces unusual two consecutive β-hydride eliminations to form 1-naphthonitrile and KH. The freshly generated KH is hydridic enough to undergo dearomative hydride addition to the resultant 1-naphthonitrile regioselectively at the C4 position to afford α-cyano benzylic carbanion, which could be functionalized by a series of electrophiles, liberating the corresponding 1,4-dihydronaphthalene-1-carbonitriles having a quaternary carbon center.

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