General and selective syn-carboxylation-trifluoromethylation of terminal alkynes: application to the late-stage modification of dehydrocholic acid. Issue 28 (19th March 2019)

• Record Type: Journal Article
• Authors: Zhang, Song-Lin; Xiao, Chang; Wan, Hai-Xing; Zhang, Xiaoming
• Is Part Of: Chemical communications. Volume 55:Issue 28(2019)
• Page Start: 4099
• Page End: 4102
• Publication Date: 2019-03-19
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c9cc01173k
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A general and selective syn -carboxylation-trifluoromethylation across the triple bond of terminal alkynes is developed by virtue of a reactive Cu(iii )–CF3 complex, which produces a broad range of biologically active trifluoromethylated enol esters with excellent regio- and stereoselectivity. Abstract : A general and selective method is developed that allows difunctionalization of terminal alkynes by a Cu(iii )–CF3 complex and a carboxylic acid regioselectively and with unusual syn -stereochemistry. This method is broadly applicable to various carboxylic acids and terminal alkynes, producing a range of biologically active trifluoromethyl enol carboxylic esters. The synthetic potential of this method is further demonstrated by the late-stage functionalization of a complex pharmaceutical compound dehydrocholic acid.