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Gold Redox Catalysis with a Selenium Cation as a Mild Oxidant |
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| Authors: | Dr Jin Wang Chiyu Wei Xuming Li Pengyi Zhao Chuan Shan Lukasz Wojtas Prof?Dr Hao Chen Prof?Dr Xiaodong Shi |
| Institution: | 1. College of Chemistry, Chemical Engineering and Material Science, Shandong Normal University, Jinan, Shandong, 250014 P. R. China
These authors contribute equally to this work.;2. Department of Chemistry, University of South Florida, Tampa, FL, 33620 USA;3. Department of Chemistry and Environmental Science, New Jersey Institute of Technology, Newark, NJ, 07102 USA |
| Abstract: | Gold-catalyzed alkyne and allene diselenations were developed. Excellent regioselectivity (trans) and good to excellent yields were achieved (up to 98 % with 2 % catalyst loading) with a wide range of substrates. Mechanistic investigation revealed the formation of a vinyl gold(I) intermediate followed by an intermolecular selenium cation migration, suggesting that a gold(I/III) redox process was successfully implemented under mild conditions. |
| Keywords: | alkyne allene diselenation gold redox catalysis mild oxidant |