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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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Detalles Bibliográficos
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
Descripción
Sumario:[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.