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Cobalt Catalyst Determines Regioselectivity in Ring Opening of Epoxides with Aryl Halides
[Image: see text] Ring-opening of epoxides furnishing either linear or branched products belongs to the group of classic transformations in organic synthesis. However, the regioselective cross-electrophile coupling of aryl epoxides with aryl halides still represents a key challenge. Herein, we repor...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2021
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8297733/ https://www.ncbi.nlm.nih.gov/pubmed/34081860 http://dx.doi.org/10.1021/jacs.1c00659 |
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author | Potrząsaj, Aleksandra Musiejuk, Mateusz Chaładaj, Wojciech Giedyk, Maciej Gryko, Dorota |
author_facet | Potrząsaj, Aleksandra Musiejuk, Mateusz Chaładaj, Wojciech Giedyk, Maciej Gryko, Dorota |
author_sort | Potrząsaj, Aleksandra |
collection | PubMed |
description | [Image: see text] Ring-opening of epoxides furnishing either linear or branched products belongs to the group of classic transformations in organic synthesis. However, the regioselective cross-electrophile coupling of aryl epoxides with aryl halides still represents a key challenge. Herein, we report that the vitamin B(12)/Ni dual-catalytic system allows for the selective synthesis of linear products under blue-light irradiation, thus complementing methodologies that give access to branched alcohols. Experimental and theoretical studies corroborate the proposed mechanism involving alkylcobalamin as an intermediate in this reaction. |
format | Online Article Text |
id | pubmed-8297733 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-82977332021-07-23 Cobalt Catalyst Determines Regioselectivity in Ring Opening of Epoxides with Aryl Halides Potrząsaj, Aleksandra Musiejuk, Mateusz Chaładaj, Wojciech Giedyk, Maciej Gryko, Dorota J Am Chem Soc [Image: see text] Ring-opening of epoxides furnishing either linear or branched products belongs to the group of classic transformations in organic synthesis. However, the regioselective cross-electrophile coupling of aryl epoxides with aryl halides still represents a key challenge. Herein, we report that the vitamin B(12)/Ni dual-catalytic system allows for the selective synthesis of linear products under blue-light irradiation, thus complementing methodologies that give access to branched alcohols. Experimental and theoretical studies corroborate the proposed mechanism involving alkylcobalamin as an intermediate in this reaction. American Chemical Society 2021-06-03 2021-06-30 /pmc/articles/PMC8297733/ /pubmed/34081860 http://dx.doi.org/10.1021/jacs.1c00659 Text en © 2021 The Authors. Published by American Chemical Society 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 | Potrząsaj, Aleksandra Musiejuk, Mateusz Chaładaj, Wojciech Giedyk, Maciej Gryko, Dorota Cobalt Catalyst Determines Regioselectivity in Ring Opening of Epoxides with Aryl Halides |
title | Cobalt
Catalyst Determines Regioselectivity in Ring
Opening of Epoxides with Aryl Halides |
title_full | Cobalt
Catalyst Determines Regioselectivity in Ring
Opening of Epoxides with Aryl Halides |
title_fullStr | Cobalt
Catalyst Determines Regioselectivity in Ring
Opening of Epoxides with Aryl Halides |
title_full_unstemmed | Cobalt
Catalyst Determines Regioselectivity in Ring
Opening of Epoxides with Aryl Halides |
title_short | Cobalt
Catalyst Determines Regioselectivity in Ring
Opening of Epoxides with Aryl Halides |
title_sort | cobalt
catalyst determines regioselectivity in ring
opening of epoxides with aryl halides |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8297733/ https://www.ncbi.nlm.nih.gov/pubmed/34081860 http://dx.doi.org/10.1021/jacs.1c00659 |
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