Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 8, Pages 2085-2089Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201310249
Keywords
disulfides; photocatalysis; quantum dots; radical reactions; thiols
Categories
Funding
- Ministry of Science and Technology of China [2013CB834804, 2013CB834505, 2014CB239402]
- National Science Foundation of China [21390404, 21090343, 91027041]
- Solar Energy Initiative of the Knowledge Innovation Program of the Chinese Academy of Sciences
- Chinese Academy of Sciences
- US National Science Foundation [CHE-1147353]
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Quantum dots (QDs) offer new and versatile ways to harvest light energy. However, there are few examples involving the utilization of QDs in organic synthesis. Visible-light irradiation of CdSe QDs was found to result in virtually quantitative coupling of a variety of thiols to give disulfides and H-2 without the need for sacrificial reagents or external oxidants. The addition of small amounts of nickel(II) salts dramatically improved the efficiency and conversion through facilitating the formation of hydrogen atoms, thereby leading to faster regeneration of the ground-state QDs. Mechanistic studies reveal that the coupling reaction occurs on the QD surfaces rather than in solution and offer a blueprint for how these QDs may be used in other photocatalytic applications. Because no sacrificial agent or oxidant is necessary and the catalyst is reusable, this method may be useful for the formation of disulfide bonds in proteins as well as in other systems sensitive to the presence of oxidants.
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