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

Pirnot, Michael T; Rankic, Danica A; Martin, David B C; MacMillan, David W C · Science · 2013

basic_science · Level V

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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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