Photoredox Activation for the Direct β-Arylation of Ketones and Aldehydes

The direct β-activation of saturated aldehydes and ketones has long been an elusive transformation. We found that photoredox catalysis in combination with organocatalysis can lead to the transient generation of 5π-electron β-enaminyl radicals from ketones and aldehydes that rapidly couple with cyano...

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Bibliographic Details
Published in:Science (American Association for the Advancement of Science) 2013-03, Vol.339 (6127), p.1593-1596
Main Authors: Pirnot, Michael T., Rankic, Danica A., Martin, David B. C., MacMillan, David W. C.
Format: Article
Language:English
Subjects:
Activation
Aldehydes
Aldehydes - chemistry
Aluminum
Amines
Anions
Bonding
Carbon
Catalysis
Catalysts
Chains
Chemistry
Electrons
Exact sciences and technology
Free radicals
Functional groups
General and physical chemistry
Ketones
Ketones - chemistry
Oxidation
Oxidation-Reduction
Photochemical Processes
Photochemistry
Physical chemistry of induced reactions (with radiations, particles and ultrasonics)
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Transformations
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Summary:The direct β-activation of saturated aldehydes and ketones has long been an elusive transformation. We found that photoredox catalysis in combination with organocatalysis can lead to the transient generation of 5π-electron β-enaminyl radicals from ketones and aldehydes that rapidly couple with cyano-substituted aryl rings at the carbonyl β-position. This mode of activation is suitable for a broad range of carbonyl β-functionalization reactions and is amenable to enantioselective catalysis.
ISSN:0036-8075
1095-9203
DOI:10.1126/science.1232993