Metal-catalyzed
(Cu, Ag, Au) reactions of alkynylphosphonates with
1-(2-aminophenyl)-2,2,2-trifluoroethan-1-ones were developed. Terminal
alkyne diethyl ethynylphosphonate reacted with ketones to give different
products depending on the catalyst used. With a CuI/PPh3 catalytic system, the formation of CF3-containing indoline
derivatives was observed with good yields. The use of AgSbF6 as a catalyst led to quinoline derivatives in high yields. The less
reactive 2-substituted ethynylphosphonates required gold complexes
as catalysts to provide the corresponding 2-aryl(alkyl) substituted
4-(trifluoromethyl)quinolin-3-ylphosphonates with good yields.