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

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 ani...

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Veröffentlicht in:Angewandte Chemie International Edition 2017-03, Vol.56 (11), p.3020-3024
Hauptverfasser: Zhao, Lei‐Min, Meng, Qing‐Yuan, Fan, Xiang‐Bing, Ye, Chen, Li, Xu‐Bing, Chen, Bin, Ramamurthy, Vaidhyanathan, Tung, Chen‐Ho, Wu, Li‐Zhu
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Sprache:eng
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Zusammenfassung: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 ing the hydrogen atom from the C−H bond of the alcohol (R1CH(OH)R2). 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. Selective oxidation of alcohols to aldehydes/ketones has been achieved with 3‐mercaptopropionic acid‐capped CdSe quantum dots (QDs) and visible light. A visible‐light‐prompted electron‐transfer reaction initiated the oxidation. The thiyl radical generated from the thiolate anion adsorbed on a CdSe QD plays a key role by ing the hydrogen atom of a C−H bond from the alcohol.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201700243