4.8 Article

Photocatalysis with Quantum Dots and Visible Light: Selective and Efficient Oxidation of Alcohols to Carbonyl Compounds through a Radical Relay Process in Water

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 11, Pages 3020-3024

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201700243

Keywords

heterogeneous catalysis; photocatalysis; selective dehydrogenation; sustainable chemistry; quantum dots

Funding

  1. Ministry of Science and Technology of China [2013CB834804, 2013CB834505, 2014CB239402]
  2. National Science Foundation of China [21390404, 91427303]
  3. Strategic Priority Research Program of the Chinese Academy of Science [XDB17030200]
  4. Chinese Academy of Sciences
  5. US National Science Foundation [CHE-1411458]
  6. Division Of Chemistry
  7. Direct For Mathematical & Physical Scien [1411458] Funding Source: National Science Foundation

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Selective oxidation of alcohols to aldehydes/ketones has been achieved with the help of 3-mercaptopropionic acid (MPA)-capped CdSe quantum dot (MPA-CdSe QD) and visible light. Visible-light-prompted electron-transfer reaction initiates the oxidation. The thiyl radical generated from the thiolate anion adsorbed on a CdSe QD plays a key role by abstracting the hydrogen atom from the C-H bond of the alcohol ((RCH)-C-1(OH)R-2). The reaction shows high efficiency, good functional group tolerance, and high site-selectivity in polyhydroxy compounds. The generality and selectivity reported here offer a new opportunity for further applications of QDs in organic transformations.

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