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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...

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Autores principales: Potrząsaj, Aleksandra, Musiejuk, Mateusz, Chaładaj, Wojciech, Giedyk, Maciej, Gryko, Dorota
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
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.
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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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