Direct β-Alkylation of Aldehydes via Photoredox Organocatalysis
Jack A. Terrett, Michael D. Clift and David W. C. MacMillan*
*Merck Center for Catalysis, Princeton University, Princeton,
New Jersey 08544, United States, Email: dmacmill
princeton.edu
J. A. Terrett, M. D. Clift, D. W. C. MacMillan, J. Am. Chem. Soc., 2014, 136, 6858-6861.
DOI: 10.1021/ja502639e
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Abstract
In a synergistical combination of photoredox catalysis and organocatalysis for the direct β-alkylation of saturated aldehydes, 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. This redox-neutral, atom-economical C-H functionalization can be achieved both inter- and intramolecularly.
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Key Words
carbonyl compounds, esters, organocatalysis, photochemistry
ID: J48-Y2014
