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General and selective syn-carboxylation-trifluoromethylation of terminal alkynes: application to the late-stage modification of dehydrocholic acid
- Zhang, Song-Lin, Xiao, Chang, Wan, Hai-Xing, Zhang, Xiaoming
- Chemical communications 2019 v.55 no.28 pp. 4099-4102
- alkynes, carboxylic acids, carboxylic esters, chemical reactions, copper, enols, regioselectivity
- 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.