Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 2, Pages 539-544Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201508060
Keywords
catalysis; electron transfer; hydrogen bonding; oxidation; quinones
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Funding
- NIH [GM043214]
- DOE [DE-SC0009565]
- NSF predoctoral fellowship
- NIH post-doctoral fellowship
- U.S. Department of Energy (DOE) [DE-SC0009565] Funding Source: U.S. Department of Energy (DOE)
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Quinones are important organic oxidants in a variety of synthetic and biological contexts, and they are susceptible to activation towards electron transfer through hydrogen bonding. Whereas this effect of hydrogen bond donors (HBDs) has been observed for Lewis basic, weakly oxidizing quinones, comparable activation is not readily achieved when more reactive and synthetically useful electron-deficient quinones are used. We have successfully employed HBD-coupled electron transfer as a strategy to activate electron-deficient quinones. A systematic investigation of HBDs has led to the discovery that certain dicationic HBDs have an exceptionally large effect on the rate and thermodynamics of electron transfer. We further demonstrate that these HBDs can be used as catalysts in a quinone-mediated model synthetic transformation.
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