Base-Induced Dehydrogenative and Dearomative Transformation of 1-Naphthylmethylamines to 1,4-Dihydronaphthalene-1-carbonitriles

[Image: see text] 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...

Descripción completa

Detalles Bibliográficos
Autores principales: Sekiguchi, Yoshiya, Pang, Jia Hao, Ng, Jia Sheng, Chen, Jiahua, Watanabe, Kohei, Takita, Ryo, Chiba, Shunsuke
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9795570/
https://www.ncbi.nlm.nih.gov/pubmed/36590271
http://dx.doi.org/10.1021/jacsau.2c00487
_version_ 1784860290590965760
author Sekiguchi, Yoshiya
Pang, Jia Hao
Ng, Jia Sheng
Chen, Jiahua
Watanabe, Kohei
Takita, Ryo
Chiba, Shunsuke
author_facet Sekiguchi, Yoshiya
Pang, Jia Hao
Ng, Jia Sheng
Chen, Jiahua
Watanabe, Kohei
Takita, Ryo
Chiba, Shunsuke
author_sort Sekiguchi, Yoshiya
collection PubMed
description [Image: see text] 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.
format Online
Article
Text
id pubmed-9795570
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-97955702022-12-29 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 JACS Au [Image: see text] 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. American Chemical Society 2022-11-30 /pmc/articles/PMC9795570/ /pubmed/36590271 http://dx.doi.org/10.1021/jacsau.2c00487 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle 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
title 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_short 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
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9795570/
https://www.ncbi.nlm.nih.gov/pubmed/36590271
http://dx.doi.org/10.1021/jacsau.2c00487
work_keys_str_mv AT sekiguchiyoshiya baseinduceddehydrogenativeanddearomativetransformationof1naphthylmethylaminesto14dihydronaphthalene1carbonitriles
AT pangjiahao baseinduceddehydrogenativeanddearomativetransformationof1naphthylmethylaminesto14dihydronaphthalene1carbonitriles
AT ngjiasheng baseinduceddehydrogenativeanddearomativetransformationof1naphthylmethylaminesto14dihydronaphthalene1carbonitriles
AT chenjiahua baseinduceddehydrogenativeanddearomativetransformationof1naphthylmethylaminesto14dihydronaphthalene1carbonitriles
AT watanabekohei baseinduceddehydrogenativeanddearomativetransformationof1naphthylmethylaminesto14dihydronaphthalene1carbonitriles
AT takitaryo baseinduceddehydrogenativeanddearomativetransformationof1naphthylmethylaminesto14dihydronaphthalene1carbonitriles
AT chibashunsuke baseinduceddehydrogenativeanddearomativetransformationof1naphthylmethylaminesto14dihydronaphthalene1carbonitriles

Ejemplares similares