Conjugated polymers as photoredox catalysts: a new catalytic system using visible light to promote aryl aldehyde pinacol couplings

The conjugated polymer poly-(p)-phenylene (PPP) was synthesized and used as a photoredox catalyst to promote pinacol coupling of aryl-aldehydes with visible light. The reaction required the use of a sacrificial electron donor (Et3N), and was accelerated by the addition of Lewis and Bronsted acids. A distinct advantage of this photocatalytic system is the robust nature of the system, which is not overly sensitive to impurities, oxygen, or temperature, and proceeds cleanly with few side reactions. As a comparison with the PPP system, the reactivity of Ru(bpy)(3)Cl-2, a popular photoredox catalyst was compared. The PPP system was superior to the Ru(bpy)(3)Cl-2 for the pinacol couplings in both rate and yield. (C) 2012 Elsevier Ltd. All rights reserved.