Work

Visible Light Promoted Site‐Specific Functionalization of α‐Acyloxy Carboxamides: Unlocking a Forbidden Chemical Space in the Passerini Reaction

Year: 2024

Type: article

Abstract: The facile generation of the α-acyloxy carboxamide radical is hereby reported for the first time, utilizing a photoredox catalyzed reaction of Passerini adducts synthesized using a 4-formyl-1,4-dihydropyridine as the carbonyl component. This radical effectively engages in a Giese reaction with a range of olefins, ultimately leading to the synthesis of novel Passerini-derived products not previously amenable to direct aldehyde-based transformations. Consequently, the resulting strategy, developed both in batch and in flow, offers a promising opportunity to expand the chemical space accessible through the Passerini reaction, virtually incorporating "impossible" aldehydes.

Source: Chemistry - A European Journal

DOI: 10.1002/chem.202402175

Authors: Francesca Brunelli, Francesca Quartieri, Ivana Miletto, Maurizio Pulici, Gianluca Papeo, Gian Cesare Tron

Institutions: Università degli Studi del Piemonte Orientale “Amedeo Avogadro”, Nerviano Medical Sciences

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,640

Funder: Università degli Studi del Piemonte Orientale