Work

Decarboxylative Allylation of Amino Alkanoic Acids and Esters via Dual Catalysis

Year: 2014

Type: article

Abstract: A combination of photoredox and palladium catalysis has been employed to facilitate the room temperature decarboxylative allylation of recalcitrant α-amino and phenylacetic allyl esters. This operationally simple process produces CO2 as the only byproduct and provides direct access to allylated alkanes. After photochemical oxidation, the carboxylate undergoes radical decarboxylation to site-specifically generate radical intermediates which undergo allylation. A radical dual catalysis mechanism is proposed. Free phenylacetic acids were also allylated utilizing similar reactions conditions.

Source: Journal of the American Chemical Society

DOI: 10.1021/ja508317j

Authors: Simon B. Lang, Kathryn M. O’Nele, Jon A. Tunge

Institution: University of Kansas

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: National Science Foundation, National Institutes of Health, National Center for Research Resources, Division of Chemistry