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Gold Redox Catalysis with a Selenium Cation as a Mild Oxidant.
Wang, Jin; Wei, Chiyu; Li, Xuming; Zhao, Pengyi; Shan, Chuan; Wojtas, Lukasz; Chen, Hao; Shi, Xiaodong.
Affiliation
  • Wang J; College of Chemistry, Chemical Engineering and Material Science, Shandong Normal University, Jinan, Shandong, 250014, P. R. China.
  • Wei C; Department of Chemistry, University of South Florida, Tampa, FL, 33620, USA.
  • Li X; Department of Chemistry, University of South Florida, Tampa, FL, 33620, USA.
  • Zhao P; Department of Chemistry and Environmental Science, New Jersey Institute of Technology, Newark, NJ, 07102, USA.
  • Shan C; Department of Chemistry, University of South Florida, Tampa, FL, 33620, USA.
  • Wojtas L; Department of Chemistry, University of South Florida, Tampa, FL, 33620, USA.
  • Chen H; Department of Chemistry and Environmental Science, New Jersey Institute of Technology, Newark, NJ, 07102, USA.
  • Shi X; Department of Chemistry, University of South Florida, Tampa, FL, 33620, USA.
Chemistry ; 26(27): 5946-5950, 2020 May 12.
Article in En | MEDLINE | ID: mdl-32037616
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.
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