Conjugated polymers as photoredox catalysts: a new catalytic system using visible light to promote aryl aldehyde pinacol couplings |
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Authors: | William D RouchMiao Zhang Ryan D McCulla |
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Institution: | Department of Chemistry, Saint Louis University, 3501 Laclede Avenue, Saint Louis, Missouri 63104, USA |
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Abstract: | 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 Brønsted 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)3Cl2, a popular photoredox catalyst was compared. The PPP system was superior to the Ru(bpy)3Cl2 for the pinacol couplings in both rate and yield. |
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Keywords: | Pinacol Poly-(p)-phenylene Visible light Photoredox catalyst Aryl aldehydes Conjugated polymer |
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