Repurposing carboxylic acids and alcohols/amines to create α-hydroxy/amino ketones

Carboxylic acids and alcohols/amines are among the most used chemicals. Combining these abundant functional groups orthogonally in organic synthesis harnesses the vast collection of commercial chemical repositories to rapidly expand chemical space. In this issue of Chem, Gutierrez, Scheidt, and co-workers present an approach utilizing carboxylic acids and alcohol/amine-derived phosphorous reagents to create α-hydroxy/amino ketones. Carboxylic acids and alcohols/amines are among the most used chemicals. Combining these abundant functional groups orthogonally in organic synthesis harnesses the vast collection of commercial chemical repositories to rapidly expand chemical space. In this issue of Chem, Gutierrez, Scheidt, and co-workers present an approach utilizing carboxylic acids and alcohol/amine-derived phosphorous reagents to create α-hydroxy/amino ketones. Visible-light-induced coupling of carboxylic acids with alcohols/amines via a phosphorous linchpin strategyPeng et al.ChemMay 10, 2023In BriefThe use of a phosphorous-based functional group in a transient intramolecular context enables the conversion of carboxylic acid and alcohols/amines, resulting in a broad range of privileged α-functionalized carbonyl compounds with high functional group tolerance and versatility. This reaction obviates the need for photocatalysts because it capitalizes on triplet excited state intermediates generated by visible light to promote a hydrogen atom transfer (HAT) coupled with a C–C bond formation. Full-Text PDF