Catalytic Access to 4-(sec-Alkyl)Anilines via 1,6-Conjugate Addition of Grignard Reagents to in Situ Generated aza-p-Quinone Methides

[Image: see text] The synthesis of aniline derivatives, common building blocks in many pharmaceuticals, agrochemicals, dyes or polymers, has been limited to reactions based on benzene-toluene-xylene derivatives (BTX) due to their ample availability. Despite the large number of existing methodologies...

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Autores principales: Zurro, Mercedes, Ge, Luo, Harutyunyan, Syuzanna R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9486948/
https://www.ncbi.nlm.nih.gov/pubmed/36053069
http://dx.doi.org/10.1021/acs.orglett.2c02786
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author Zurro, Mercedes
Ge, Luo
Harutyunyan, Syuzanna R.
author_facet Zurro, Mercedes
Ge, Luo
Harutyunyan, Syuzanna R.
author_sort Zurro, Mercedes
collection PubMed
description [Image: see text] The synthesis of aniline derivatives, common building blocks in many pharmaceuticals, agrochemicals, dyes or polymers, has been limited to reactions based on benzene-toluene-xylene derivatives (BTX) due to their ample availability. Despite the large number of existing methodologies, the synthesis of chiral 4-(sec-alkyl)anilines has not been accomplished so far. In this work, a tandem strategy based on the generation of a reactive aza-p-quinone methide (aza-p-QM) intermediate followed by Cu(I)-catalyzed addition of Grignard reagents has been developed.
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spelling pubmed-94869482022-09-21 Catalytic Access to 4-(sec-Alkyl)Anilines via 1,6-Conjugate Addition of Grignard Reagents to in Situ Generated aza-p-Quinone Methides Zurro, Mercedes Ge, Luo Harutyunyan, Syuzanna R. Org Lett [Image: see text] The synthesis of aniline derivatives, common building blocks in many pharmaceuticals, agrochemicals, dyes or polymers, has been limited to reactions based on benzene-toluene-xylene derivatives (BTX) due to their ample availability. Despite the large number of existing methodologies, the synthesis of chiral 4-(sec-alkyl)anilines has not been accomplished so far. In this work, a tandem strategy based on the generation of a reactive aza-p-quinone methide (aza-p-QM) intermediate followed by Cu(I)-catalyzed addition of Grignard reagents has been developed. American Chemical Society 2022-09-02 2022-09-16 /pmc/articles/PMC9486948/ /pubmed/36053069 http://dx.doi.org/10.1021/acs.orglett.2c02786 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Zurro, Mercedes
Ge, Luo
Harutyunyan, Syuzanna R.
Catalytic Access to 4-(sec-Alkyl)Anilines via 1,6-Conjugate Addition of Grignard Reagents to in Situ Generated aza-p-Quinone Methides
title Catalytic Access to 4-(sec-Alkyl)Anilines via 1,6-Conjugate Addition of Grignard Reagents to in Situ Generated aza-p-Quinone Methides
title_full Catalytic Access to 4-(sec-Alkyl)Anilines via 1,6-Conjugate Addition of Grignard Reagents to in Situ Generated aza-p-Quinone Methides
title_fullStr Catalytic Access to 4-(sec-Alkyl)Anilines via 1,6-Conjugate Addition of Grignard Reagents to in Situ Generated aza-p-Quinone Methides
title_full_unstemmed Catalytic Access to 4-(sec-Alkyl)Anilines via 1,6-Conjugate Addition of Grignard Reagents to in Situ Generated aza-p-Quinone Methides
title_short Catalytic Access to 4-(sec-Alkyl)Anilines via 1,6-Conjugate Addition of Grignard Reagents to in Situ Generated aza-p-Quinone Methides
title_sort catalytic access to 4-(sec-alkyl)anilines via 1,6-conjugate addition of grignard reagents to in situ generated aza-p-quinone methides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9486948/
https://www.ncbi.nlm.nih.gov/pubmed/36053069
http://dx.doi.org/10.1021/acs.orglett.2c02786
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