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Decarboxylative Alkyl Coupling Promoted by NADH and Blue Light.

ABSTRACT: Photoexcited dihydronicotinamides like NADH and analogues have been found to generate alkyl radicals upon reductive decarboxylation of redox-active esters without auxiliary photocatalysts. This principle allowed aliphatic photocoupling between redox-active carboxylate derivatives and electron-poor olefins, displaying surprising water and air-tolerance and unusually high coupling rates in dilute conditions. The orthogonality of the reaction in the presence of other carboxylic acids and its utility in the functionalization of DNA is presented, notably using visible light in combination with NADH, the ubiquitous reductant of life.

SUBMITTER: Chowdhury R

PROVIDER: S-EPMC7705967 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Decarboxylative Alkyl Coupling Promoted by NADH and Blue Light.

Chowdhury Rajdip R Yu Zhunzhun Z Tong My Linh ML Kohlhepp Stefanie V SV Yin Xiang X Mendoza Abraham A

Journal of the American Chemical Society 20201030 47

Photoexcited dihydronicotinamides like NADH and analogues have been found to generate alkyl radicals upon reductive decarboxylation of redox-active esters without auxiliary photocatalysts. This principle allowed aliphatic photocoupling between redox-active carboxylate derivatives and electron-poor olefins, displaying surprising water and air-tolerance and unusually high coupling rates in dilute conditions. The orthogonality of the reaction in the presence of other carboxylic acids and its utilit ...[more]

PMID: 33125842

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