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Decarboxylative allylation of amino alkanoic acids and esters via dual catalysis.

ABSTRACT: A combination of photoredox and palladium catalysis has been employed to facilitate the room temperature decarboxylative allylation of recalcitrant ?-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.

SUBMITTER: Lang SB

PROVIDER: S-EPMC4183636 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

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Decarboxylative allylation of amino alkanoic acids and esters via dual catalysis.

Lang Simon B SB O'Nele Kathryn M KM Tunge Jon A JA

Journal of the American Chemical Society 20140922 39

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 i ...[more]

PMID: 25228064

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