Facilitating [2+2] Photocycloadditions by Promoting Oxygen Tolerance and Substrate Activation in Water

Abstract

AbstractMicellar photocatalysis has been used to overcome oxygen quenching and enable a [2+2] photocycloaddition through triplet‐energy transfer in water under aerobic conditions. The cheap and commercially available self‐assembling sodium dodecyl sulfate (SDS) micelles were found to increase the oxygen tolerance of a typically oxygen‐sensitive reaction. Furthermore, the use of the micellar solution was found to activate α,β‐unsaturated carbonyl compounds to energy transfer and allow [2+2] photocycloadditions to take place. Our preliminary studies of micellar effects on energy‐transfer‐based reactions demonstrate the reaction between α,β‐unsaturated carbonyl compounds and activated alkenes in a mixture of SDS, water and [Ru(bpy)3](PF6)2.