Direct β‑Alkylation of Aldehydes via Photoredox Organocatalysis

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...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2014-05, Vol.136 (19), p.6858-6861
Main Authors: Terrett, Jack A, Clift, Michael D, MacMillan, David W. C
Format: Article
Language:English
Subjects:
Activated
Aldehydes
Aldehydes - chemistry
Alkylation
Catalysis
Communication
Cyclization
Oxidation-Reduction
Pathways
Photochemical Processes
Quenching
Radicals
Spectroscopic analysis
Spectroscopy
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja502639e