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Direct β-alkylation of aldehydes via photoredox organocatalysis.

ABSTRACT: Direct β-alkylation of saturated aldehydes has been accomplished by synergistically combining photoredox catalysis and organocatalysis. Photon-induced enamine oxidation provides an activated β-enaminyl radical intermediate, which readily combines with a wide range of Michael acceptors to produce β-alkyl aldehydes in a highly efficient manner. Furthermore, this redox-neutral, atom-economical C-H functionalization protocol can be achieved both inter- and intramolecularly. Mechanistic studies by various spectroscopic methods suggest that a reductive quenching pathway is operable.

SUBMITTER: Terrett JA

PROVIDER: S-EPMC4333594 | biostudies-literature | 2014 May

REPOSITORIES: biostudies-literature

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Direct β-alkylation of aldehydes via photoredox organocatalysis.

Terrett Jack A JA Clift Michael D MD MacMillan David W C DW

Journal of the American Chemical Society 20140429 19

Direct β-alkylation of saturated aldehydes has been accomplished by synergistically combining photoredox catalysis and organocatalysis. Photon-induced enamine oxidation provides an activated β-enaminyl radical intermediate, which readily combines with a wide range of Michael acceptors to produce β-alkyl aldehydes in a highly efficient manner. Furthermore, this redox-neutral, atom-economical C-H functionalization protocol can be achieved both inter- and intramolecularly. Mechanistic studies by va ...[more]

PMID: 24754456

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