Work

Selective Radical–Radical Cross-Couplings: Design of a Formal β-Mannich Reaction

Year: 2015

Type: article

Abstract: A direct β-coupling of cyclic ketones with imines has been accomplished via the synergistic combination of photoredox catalysis and organocatalysis. Transient β-enaminyl radicals derived from ketones via enamine and oxidative photoredox catalysis readily combine with persistent α-amino radicals in a highly selective hetero radical-radical coupling. This novel pathway to γ-aminoketones is predicated upon the use of DABCO as both a base and an electron transfer agent. This protocol also formally allows for the direct synthesis of β-Mannich products via a chemoselective three-component coupling of aryl aldehydes, amines, and ketones.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.5b05376

Authors: Jenna L. Jeffrey, Filip R. Petronijević, David W. C. MacMillan

Institution: Princeton University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute of General Medical Sciences

Awards: Photoredox Catalysis Applications in Organometallics and Chemical Biology, G1588828791, G30908861, G4617881979, Beta Functionalization of Aldehydes and Ketones Using Photoredox Organocatalysis