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

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

Chemistry

Research output: Contribution to journal › Article › peer-review

411 Scopus citations

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.

Original language	English (US)
Pages (from-to)	1593-1596
Number of pages	4
Journal	Science
Volume	340
Issue number	6127
DOIs	https://doi.org/10.1126/science.1232993
State	Published - Mar 29 2013

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10.1126/science.1232993

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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.",

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AU - Rankic, Danica A.

AU - Martin, David B.C.

AU - MacMillan, David W.C.

PY - 2013/3/29

Y1 - 2013/3/29

N2 - 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.

AB - 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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Photoredox activation for the direct β-arylation of ketones and aldehydes

Abstract

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