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Cobalt Catalyst Determines Regioselectivity in Ring Opening of Epoxides with Aryl Halides.

ABSTRACT: 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 B₁₂/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.

SUBMITTER: Potrzasaj A

PROVIDER: S-EPMC8297733 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature

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Cobalt Catalyst Determines Regioselectivity in Ring Opening of Epoxides with Aryl Halides.

Potrząsaj Aleksandra A Musiejuk Mateusz M Chaładaj Wojciech W Giedyk Maciej M Gryko Dorota D

Journal of the American Chemical Society 20210603 25

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<sub>12</sub>/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. Exp ...[more]

PMID: 34081860

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