Litcius/Paper detail

Organocatalyzed Photoelectrochemistry for the Generation of Acyl and Phosphoryl Radicals through Hydrogen Atom-Transfer Process

Hong He, Cai-Mi Pan, Zhong‐Wei Hou, Manman Sun, Lei Wang

2024The Journal of Organic Chemistry15 citationsDOI

Abstract

An organocatalyzed photoelectrochemical method for the generation of acyl and phosphoryl radicals from formamides, aldehydes, and phosphine oxides has been developed. This protocol utilizes 9,10-phenanthrenequinone (PQ) as both a molecular catalyst and a hydrogen atom-transfer (HAT) reagent, eliminating the requirement for external metal-based reagents, HAT reagents, and oxidants. The generated acyl radicals can be applied to a range of radical-mediated transformation reactions, including C–H carbamoylation of heteroarenes, intermolecular tandem radical cyclization of CF 3 -substituted N -arylacrylamides, as well as intramolecular cyclization reactions. The use of acyl radicals in these transformations offers an efficient and sustainable approach to accessing structurally diverse carbonyl compounds.

Topics & Concepts

Hydrogen atomChemistryPhotoelectrochemistryRadicalProcess (computing)HydrogenPhotochemistryOrganic chemistryPhysical chemistryElectrochemistryComputer scienceAlkylOperating systemElectrodeRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesFluorine in Organic Chemistry
Organocatalyzed Photoelectrochemistry for the Generation of Acyl and Phosphoryl Radicals through Hydrogen Atom-Transfer Process | Litcius