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Visible-light-induced coupling of carboxylic acids with alcohols/amines via a phosphorous linchpin strategy.

ABSTRACT: The combination of activated carboxylic acids and alcohols/amines to access esters and amides, respectively, is a cornerstone of organic chemistry and has been well developed over the past century. These dehydrations are extensively used in medicinal chemistry and natural product synthesis due to the prevalence of these functional groups in bioactive molecules. Here, we report a divergent process from the expected ester/amide outcomes through a light-induced coupling of activated carboxylic acids and alcohols/amines to efficiently prepare α-hydroxy/amino ketones or β-ketophosphonates via single-electron chemistry. A phosphorus linchpin strategy allows for the combination of these simple reagents through an intramolecular triplet state radical process, thereby enabling new carbon-carbon bond formation.

SUBMITTER: Peng Q

PROVIDER: S-EPMC10399973 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature

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Visible-light-induced coupling of carboxylic acids with alcohols/amines via a phosphorous linchpin strategy.

Peng Qiupeng Q Gogoi Achyut Ranjan AR Rentería-Gómez Ángel Á Gutierrez Osvaldo O Scheidt Karl A KA

Chem 20230510 7

The combination of activated carboxylic acids and alcohols/amines to access esters and amides, respectively, is a cornerstone of organic chemistry and has been well developed over the past century. These dehydrations are extensively used in medicinal chemistry and natural product synthesis due to the prevalence of these functional groups in bioactive molecules. Here, we report a divergent process from the expected ester/amide outcomes through a light-induced coupling of activated carboxylic acid ...[more]

PMID: 37547627

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