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

Micellar 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 alpha,beta-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 alpha,beta-unsaturated carbonyl compounds and activated alkenes in a mixture of SDS, water and [Ru(bpy)(3)](PF6)(2).

Automated summary

Micellar photocatalysis enables a [2+2] photocycloaddition in water under aerobic conditions by overcoming oxygen quenching through triplet-energy transfer. The use of self-assembling sodium dodecyl sulfate (SDS) micelles improves the oxygen tolerance of oxygen-sensitive reactions and activates alpha,beta-unsaturated carbonyl compounds for energy transfer. Preliminary studies demonstrate the reaction between these compounds and activated alkenes in an SDS, water, and [Ru(bpy)(3)](PF6)(2) mixture.