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A practical and sustainable two-component Minisci alkylation via photo-induced EDA-complex activation.

ABSTRACT: An operationally simple, open-air, and efficient light-mediated Minisci C-H alkylation method is described, based on the formation of an electron donor-acceptor (EDA) complex between nitrogen-containing heterocycles and redox-active esters. In contrast to previously reported protocols, this method does not require a photocatalyst, an external single electron transfer agent, or an oxidant additive. Achieved under mildly acidic and open-air conditions, the reaction incorporates primary-, secondary-, and tertiary radicals, including bicyclo[1.1.1]pentyl (BCP) radicals, along with various heterocycles to generate Minisci alkylation products in moderate to good yields. Additionally, the method is exploited to generate a stereo-enriched, hetereoaryl-substituted carbohydrate.

SUBMITTER: Sharique M

PROVIDER: S-EPMC9116295 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature

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A practical and sustainable two-component Minisci alkylation via photo-induced EDA-complex activation.

Sharique Mohammed M Majhi Jadab J Dhungana Roshan K RK Kammer Lisa Marie LM Krumb Matthias M Lipp Alexander A Romero Eugénie E Molander Gary A GA

Chemical science 20220426 19

An operationally simple, open-air, and efficient light-mediated Minisci C-H alkylation method is described, based on the formation of an electron donor-acceptor (EDA) complex between nitrogen-containing heterocycles and redox-active esters. In contrast to previously reported protocols, this method does not require a photocatalyst, an external single electron transfer agent, or an oxidant additive. Achieved under mildly acidic and open-air conditions, the reaction incorporates primary-, secondary ...[more]

PMID: 35694363

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