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Title: Base-induced dehydrogenative and dearomative transformation of 1-naphthylmethylamines to 1,4-dihydronaphthalene-1-carbonitriles
Authors: Sekiguchi, Yoshiya
Pang, Jia Hao
Ng, Jia Sheng
Chen, Jiahua
Watanabe, Kohei
Takita, Ryo
Chiba, Shunsuke
Keywords: Engineering::Chemical engineering
Issue Date: 2022
Source: Sekiguchi, Y., Pang, J. H., Ng, J. S., Chen, J., Watanabe, K., Takita, R. & Chiba, S. (2022). Base-induced dehydrogenative and dearomative transformation of 1-naphthylmethylamines to 1,4-dihydronaphthalene-1-carbonitriles. JACS Au, 2(12), 2758-2764.
Project: MOE2019-T2-1-089 
Journal: JACS Au 
Abstract: 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.
ISSN: 2691-3704
DOI: 10.1021/jacsau.2c00487
Schools: School of Chemistry, Chemical Engineering and Biotechnology 
Rights: © 2022 The Authors. Published by American Chemical Society. This is an open-access article distributed under the terms of the Creative Commons Attribution License.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:CCEB Journal Articles

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