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

by Martin, David B. C. , Pirnot, Michael T. , MacMillan, David W. C. , Rankic, Danica A.

in Activation / Aldehydes / Aldehydes - chemistry / Aluminum / Amines / Anions / Bonding / Carbon / carbonyl compounds / Catalysis / Catalysts / Chains / Chemistry / Electrons / Exact sciences and technology / Free radicals / Functional groups / General and physical chemistry / Ketones / Ketones - chemistry / Oxidation / Oxidation-Reduction / oxygen / Photochemical Processes / Photochemistry / Physical chemistry of induced reactions (with radiations, particles and ultrasonics) / redox reactions / Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry / Transformations

2013

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

by Martin, David B. C. , Pirnot, Michael T. , MacMillan, David W. C. , Rankic, Danica A.

2013

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

by Martin, David B. C. , Pirnot, Michael T. , MacMillan, David W. C. , Rankic, Danica A.

2013

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Journal Article

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

Martin, David B. C.,

Pirnot, Michael T.,

MacMillan, David W. C.,

Rankic, Danica A.

2013

Overview

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.

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Publisher

American Association for the Advancement of Science

Subject

Activation

/ Aldehydes

/ Aldehydes - chemistry

/ Aluminum

/ Amines

/ Anions

/ Bonding