Bifunctional Copper-Based Photocatalyst for Reductive Pinacol-Type Couplings
A bifunctional copper-based photocatalyst has been prepared that employs a pyrazole-pyridine ligand incorporating a sulfonamide moiety that functions as an intramolecular hydrogen-bond donor for a photochemical PCET process. In typical reductive PCET processes, the photocatalyst and H-bond donor mus...
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Published in | ACS catalysis Vol. 9; no. 10; pp. 9458 - 9464 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
American Chemical Society
04.10.2019
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Subjects | |
Online Access | Get full text |
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Summary: | A bifunctional copper-based photocatalyst has been prepared that employs a pyrazole-pyridine ligand incorporating a sulfonamide moiety that functions as an intramolecular hydrogen-bond donor for a photochemical PCET process. In typical reductive PCET processes, the photocatalyst and H-bond donor must have an appropriate redox potential and pK a, respectively, to promote the PCET. When working in concert in a bifunctional catalyst such as Cu(pypzs)(BINAP)BF4, the pK a of the H-bond donor can have an acidity that is orders of magnitude less and still efficiently promote the PCET process. A reductive pinacol-type coupling can be performed using a base-metal derived photocatalyst to afford valuable diols (24 examples, 46–99% yield), from readily available aldehydes and ketones. |
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ISSN: | 2155-5435 2155-5435 |
DOI: | 10.1021/acscatal.9b01718 |