C(sp(2))–H Hydroxylation via Catalytic 1,4-Ni Migration with N(2)O

[Image: see text] Herein, we report a Ni-catalyzed C(sp(2))–H hydroxylation of aryl bromides with N(2)O as an oxygen-atom donor. The reaction is enabled by a 1,4-Ni translocation that results in ipso/ortho difunctionalized products. Regioselectivity and stereocontrol are dictated by a judicious choi...

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Autores principales: Zhang, Huihui, Rodrigalvarez, Jesus, Martin, Ruben
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10586377/
https://www.ncbi.nlm.nih.gov/pubmed/37531410
http://dx.doi.org/10.1021/jacs.3c07018
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author Zhang, Huihui
Rodrigalvarez, Jesus
Martin, Ruben
author_facet Zhang, Huihui
Rodrigalvarez, Jesus
Martin, Ruben
author_sort Zhang, Huihui
collection PubMed
description [Image: see text] Herein, we report a Ni-catalyzed C(sp(2))–H hydroxylation of aryl bromides with N(2)O as an oxygen-atom donor. The reaction is enabled by a 1,4-Ni translocation that results in ipso/ortho difunctionalized products. Regioselectivity and stereocontrol are dictated by a judicious choice of the ligand backbone, thus giving access to either carbonyl or phenol derivatives and offering an opportunity to repurpose hazardous substances en route to valuable oxygen-containing building blocks.
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spelling pubmed-105863772023-10-20 C(sp(2))–H Hydroxylation via Catalytic 1,4-Ni Migration with N(2)O Zhang, Huihui Rodrigalvarez, Jesus Martin, Ruben J Am Chem Soc [Image: see text] Herein, we report a Ni-catalyzed C(sp(2))–H hydroxylation of aryl bromides with N(2)O as an oxygen-atom donor. The reaction is enabled by a 1,4-Ni translocation that results in ipso/ortho difunctionalized products. Regioselectivity and stereocontrol are dictated by a judicious choice of the ligand backbone, thus giving access to either carbonyl or phenol derivatives and offering an opportunity to repurpose hazardous substances en route to valuable oxygen-containing building blocks. American Chemical Society 2023-08-02 /pmc/articles/PMC10586377/ /pubmed/37531410 http://dx.doi.org/10.1021/jacs.3c07018 Text en © 2023 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 Zhang, Huihui
Rodrigalvarez, Jesus
Martin, Ruben
C(sp(2))–H Hydroxylation via Catalytic 1,4-Ni Migration with N(2)O
title C(sp(2))–H Hydroxylation via Catalytic 1,4-Ni Migration with N(2)O
title_full C(sp(2))–H Hydroxylation via Catalytic 1,4-Ni Migration with N(2)O
title_fullStr C(sp(2))–H Hydroxylation via Catalytic 1,4-Ni Migration with N(2)O
title_full_unstemmed C(sp(2))–H Hydroxylation via Catalytic 1,4-Ni Migration with N(2)O
title_short C(sp(2))–H Hydroxylation via Catalytic 1,4-Ni Migration with N(2)O
title_sort c(sp(2))–h hydroxylation via catalytic 1,4-ni migration with n(2)o
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10586377/
https://www.ncbi.nlm.nih.gov/pubmed/37531410
http://dx.doi.org/10.1021/jacs.3c07018
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