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

Michael T PIRNOT; Danica A RANKIC; David B. C MARTIN; David W. C MACMILLAN

doi:10.1126/science.1232993

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

Journal article

Peer reviewed

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

Michael T PIRNOT, Danica A RANKIC, David B. C MARTIN and David W. C MACMILLAN

Science (American Association for the Advancement of Science), Vol.339(6127), pp.1593-1596

2013

DOI: 10.1126/science.1232993

PMCID: PMC3723331

PMID: 23539600

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Abstract

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.

Photochemistry

Chemistry

Physical chemistry of induced reactions (with radiations, particles and ultrasonics)

Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry

Exact sciences and technology

General and physical chemistry

Catalysis

Details

Title: Subtitle: Photoredox Activation for the Direct β-Arylation of Ketones and Aldehydes
Creators: Michael T PIRNOT - Merck Center for Catalysis, Department of Chemistry, Princeton University, Princeton, NJ 08544, United States
Danica A RANKIC - Merck Center for Catalysis, Department of Chemistry, Princeton University, Princeton, NJ 08544, United States
David B. C MARTIN - Merck Center for Catalysis, Department of Chemistry, Princeton University, Princeton, NJ 08544, United States
David W. C MACMILLAN - Merck Center for Catalysis, Department of Chemistry, Princeton University, Princeton, NJ 08544, United States
Resource Type: Journal article
Publication Details: Science (American Association for the Advancement of Science), Vol.339(6127), pp.1593-1596
Publisher: American Association for the Advancement of Science; Washington, DC
DOI: 10.1126/science.1232993
PMID: 23539600
PMCID: PMC3723331
ISSN: 0036-8075
eISSN: 1095-9203
Language: English
Date published: 2013
Academic Unit: Iowa Neuroscience Institute; Chemistry
Record Identifier: 9984065856102771

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