Copper-Catalyzed Cross-Coupling of Thiols, Alcohols, and Oxygen for the Synthesis of Esters

Author: Lim Seungyeon   Ji Miran   Wang Xi   Lee Chan   Jang Hye-Young  

Publisher: Blackwell Publishing

E-ISSN: 1099-0690|2015|3|591-595

ISSN: 1434-193X

Source: European Journal of Organic Chemistry, Vol.2015, Iss.3, 2015-01, pp. : 591-595

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Abstract

Copper-catalyzed, one-pot, three-component coupling reactions using thiols, alcohols, and oxygen to form a variety of esters in good yields were studied. In the presence of easily oxidized benzylic and allylic alcohols, thiols were selectively oxidized to form thionoesters, which underwent facile S/O exchange to afford esters. Thiols may be used as an alternative benzoyl source under mild aerobic conditions. Copper-catalyzed coupling of thiols, alcohols, and oxygen provided a variety of esters through S/O exchange of thionoester intermediates