Decarboxylative Cross-Acyl Coupling of Carboxylic Acids with Aldehydes Enabled by Nickel/Photoredox Catalysis

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: 147(19), P. 15929 - 15935

Published: April 25, 2025

We present a general method for accessing unsymmetrical alkyl-aryl and alkyl-alkyl ketones via nickel/photoredox-catalyzed decarboxylative cross-acyl coupling reactions between carboxylic acids aldehydes without the need an additional preactivation procedure. Specifically, by using peroxide as both oxidant hydrogen atom transfer (HAT) reagent, we achieved unprecedented combination of oxidative single electron (SET) carboxylates HAT aldehydes, in which generated alkyl acyl radicals were chemoselectively coupled nickel catalysis. This features broad substrate scope with good functional group compatibility offers new access to structurally diverse ketones.

Language: Английский

Coupling of Acyl Radical Precursors with 2-Azaallyl Anions for the Synthesis of α-Amino Ketones

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 1, 2025

A novel transition-metal-free radical coupling of 2-azaallyl anions for the synthesis α-amino ketones has been developed. Easily accessible thioesters and undergo single electron transfer (SET) to generate acyl radicals, which participate in intermolecular with good functional group tolerance yields (31 examples, up 98% yield). telescoped gram-scale derivatization product illustrate potential synthetic utility this method. Radical trapping clock experiments support proposed pathway between generated radical.

Language: Английский