Bifunctional Copper-Based Photocatalyst for Reductive Pinacol-Type Couplings
2019; American Chemical Society; Volume: 9; Issue: 10 Linguagem: Inglês
10.1021/acscatal.9b01718
ISSN2155-5435
AutoresAntoine Caron, Émilie Morin, Shawn K. Collins,
Tópico(s)Sulfur-Based Synthesis Techniques
ResumoA 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 pKa, respectively, to promote the PCET. When working in concert in a bifunctional catalyst such as Cu(pypzs)(BINAP)BF4, the pKa 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.
Referência(s)