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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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

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spelling	sg-ntu-dr.10356-1644892023-06-21T07:36:17Z Base-induced dehydrogenative and dearomative transformation of 1-naphthylmethylamines to 1,4-dihydronaphthalene-1-carbonitriles Sekiguchi, Yoshiya Pang, Jia Hao Ng, Jia Sheng Chen, Jiahua Watanabe, Kohei Takita, Ryo Chiba, Shunsuke School of Chemistry, Chemical Engineering and Biotechnology Engineering::Chemical engineering Dearomatization Beta-Hydride Elimination 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. Ministry of Education (MOE) Nanyang Technological University Published version This work was supported by funding from Nanyang Technological University (NTU) (for S.C.) and the Singapore Ministry of Education (Academic Research Fund Tier 2: MOE2019-T2-1-089 for S.C.) as well as the Naito Foundation (for R.T.). 2023-01-30T02:24:16Z 2023-01-30T02:24:16Z 2022 Journal Article 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. https://dx.doi.org/10.1021/jacsau.2c00487 2691-3704 https://hdl.handle.net/10356/164489 10.1021/jacsau.2c00487 36590271 2-s2.0-85143488331 12 2 2758 2764 en MOE2019-T2-1-089 JACS Au © 2022 The Authors. Published by American Chemical Society. This is an open-access article distributed under the terms of the Creative Commons Attribution License. application/pdf
institution	Nanyang Technological University
building	NTU Library
continent	Asia
country	Singapore Singapore
content_provider	NTU Library
collection	DR-NTU
language	English
topic	Engineering::Chemical engineering Dearomatization Beta-Hydride Elimination
spellingShingle	Engineering::Chemical engineering Dearomatization Beta-Hydride Elimination Sekiguchi, Yoshiya Pang, Jia Hao Ng, Jia Sheng Chen, Jiahua Watanabe, Kohei Takita, Ryo Chiba, Shunsuke Base-induced dehydrogenative and dearomative transformation of 1-naphthylmethylamines to 1,4-dihydronaphthalene-1-carbonitriles
description	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.
author2	School of Chemistry, Chemical Engineering and Biotechnology
author_facet	School of Chemistry, Chemical Engineering and Biotechnology Sekiguchi, Yoshiya Pang, Jia Hao Ng, Jia Sheng Chen, Jiahua Watanabe, Kohei Takita, Ryo Chiba, Shunsuke
format	Article
author	Sekiguchi, Yoshiya Pang, Jia Hao Ng, Jia Sheng Chen, Jiahua Watanabe, Kohei Takita, Ryo Chiba, Shunsuke
author_sort	Sekiguchi, Yoshiya
title	Base-induced dehydrogenative and dearomative transformation of 1-naphthylmethylamines to 1,4-dihydronaphthalene-1-carbonitriles
title_short	Base-induced dehydrogenative and dearomative transformation of 1-naphthylmethylamines to 1,4-dihydronaphthalene-1-carbonitriles
title_full	Base-induced dehydrogenative and dearomative transformation of 1-naphthylmethylamines to 1,4-dihydronaphthalene-1-carbonitriles
title_fullStr	Base-induced dehydrogenative and dearomative transformation of 1-naphthylmethylamines to 1,4-dihydronaphthalene-1-carbonitriles
title_full_unstemmed	Base-induced dehydrogenative and dearomative transformation of 1-naphthylmethylamines to 1,4-dihydronaphthalene-1-carbonitriles
title_sort	base-induced dehydrogenative and dearomative transformation of 1-naphthylmethylamines to 1,4-dihydronaphthalene-1-carbonitriles
publishDate	2023
url	https://hdl.handle.net/10356/164489
_version_	1772828373954854912

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

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