Gold Redox Catalysis with a Selenium Cation as a Mild Oxidant

Jin Wang; Chiyu Wei; Xuming Li; Pengyi Zhao; Chuan Shan; Lukasz Wojtas; Hao Chen; Xiaodong Shi

doi:10.1002/chem.202000166

Gold Redox Catalysis with a Selenium Cation as a Mild Oxidant

Chemistry. 2020 May 12;26(27):5946-5950. doi: 10.1002/chem.202000166. Epub 2020 Apr 14.

Authors

Jin Wang¹, Chiyu Wei², Xuming Li², Pengyi Zhao³, Chuan Shan², Lukasz Wojtas², Hao Chen³, Xiaodong Shi²

Affiliations

¹ College of Chemistry, Chemical Engineering and Material Science, Shandong Normal University, Jinan, Shandong, 250014, P. R. China.
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.

Abstract

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