PubAg

Main content area

General and selective syn-carboxylation-trifluoromethylation of terminal alkynes: application to the late-stage modification of dehydrocholic acid

Author:
Zhang, Song-Lin, Xiao, Chang, Wan, Hai-Xing, Zhang, Xiaoming
Source:
Chemical communications 2019 v.55 no.28 pp. 4099-4102
ISSN:
1364-548X
Subject:
alkynes, carboxylic acids, carboxylic esters, chemical reactions, copper, enols, regioselectivity
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.
Agid:
6363385