Copper-Catalyzed Borylation of Styrenes by 1,8-Diaminonaphthalene-Protected Diboronic Acid

[Image: see text] We report a concise synthesis of 1,8-diaminonaphthalene-protected diboronic acid (B(2)(dan)(2)), which is a promising borylating agent. B(2)(dan)(2) is a bench-stable compound, and it could be utilized for Cu-catalyzed borylation of styrene derivatives. The reaction proceeded in a...

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Autores principales: Yasuda, Taiga, Yoshigoe, Yusuke, Saito, Shinichi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10071482/
https://www.ncbi.nlm.nih.gov/pubmed/36947669
http://dx.doi.org/10.1021/acs.orglett.3c00451
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author Yasuda, Taiga
Yoshigoe, Yusuke
Saito, Shinichi
author_facet Yasuda, Taiga
Yoshigoe, Yusuke
Saito, Shinichi
author_sort Yasuda, Taiga
collection PubMed
description [Image: see text] We report a concise synthesis of 1,8-diaminonaphthalene-protected diboronic acid (B(2)(dan)(2)), which is a promising borylating agent. B(2)(dan)(2) is a bench-stable compound, and it could be utilized for Cu-catalyzed borylation of styrene derivatives. The reaction proceeded in a highly selective manner, and the products were isolated in up to 97% yields. Mechanistic studies revealed that a borate species would be a key intermediate for the borylation reaction.
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spelling pubmed-100714822023-04-05 Copper-Catalyzed Borylation of Styrenes by 1,8-Diaminonaphthalene-Protected Diboronic Acid Yasuda, Taiga Yoshigoe, Yusuke Saito, Shinichi Org Lett [Image: see text] We report a concise synthesis of 1,8-diaminonaphthalene-protected diboronic acid (B(2)(dan)(2)), which is a promising borylating agent. B(2)(dan)(2) is a bench-stable compound, and it could be utilized for Cu-catalyzed borylation of styrene derivatives. The reaction proceeded in a highly selective manner, and the products were isolated in up to 97% yields. Mechanistic studies revealed that a borate species would be a key intermediate for the borylation reaction. American Chemical Society 2023-03-22 /pmc/articles/PMC10071482/ /pubmed/36947669 http://dx.doi.org/10.1021/acs.orglett.3c00451 Text en © 2023 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 Yasuda, Taiga
Yoshigoe, Yusuke
Saito, Shinichi
Copper-Catalyzed Borylation of Styrenes by 1,8-Diaminonaphthalene-Protected Diboronic Acid
title Copper-Catalyzed Borylation of Styrenes by 1,8-Diaminonaphthalene-Protected Diboronic Acid
title_full Copper-Catalyzed Borylation of Styrenes by 1,8-Diaminonaphthalene-Protected Diboronic Acid
title_fullStr Copper-Catalyzed Borylation of Styrenes by 1,8-Diaminonaphthalene-Protected Diboronic Acid
title_full_unstemmed Copper-Catalyzed Borylation of Styrenes by 1,8-Diaminonaphthalene-Protected Diboronic Acid
title_short Copper-Catalyzed Borylation of Styrenes by 1,8-Diaminonaphthalene-Protected Diboronic Acid
title_sort copper-catalyzed borylation of styrenes by 1,8-diaminonaphthalene-protected diboronic acid
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10071482/
https://www.ncbi.nlm.nih.gov/pubmed/36947669
http://dx.doi.org/10.1021/acs.orglett.3c00451
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