CuBr2 catalyzed alkynylation of tertiary methylamine with terminal alkyne using aqueous TBHP under mild conditions

Au(I)-Catalyzed Regioselective Hydrofluorination of Propargylamines Using Aqueous HF

“…More importantly, we recognized that the newly developed hydrofluorination method could provide opportunities to rapidly access fluorine-containing analogues of allylamine drugs. For example, the hydrofluorination of readily accessible propargylamine derived from copper-catalyzed couping of N,N-dimethyl-1-(naphthalen-1-yl)methanamine with phenylacetylene 22 provided the antifungal drug naftifine analogue (2p) in 71% yield with exclusive stereoselectivety. It is noteworthy that both Toste 14b and Wang 16c developed the synthesis of the naftifine analogue (2p) based on goldcatalyzed hydrofluorination of alkynes.…”

“…To assess the feasibility of the designed regioselective hydrofluorination of alkynes, readily accessible N -methyl- N -(3-phenylprop-2-yn-1-yl)­cyclohexanamine ( 1a ) were chosen as the model substrates. First, Et 3 N·3HF and 40% aqueous HF were tested as sources of HF using JohnPhosAuNTf 2 as the catalyst in toluene at 50 °C.…”

“…3-Fluoroallylamines are useful building blocks for the construction of various fluorocontaining compounds, 21 which are generally synthesized via the hydrofluorination of alkynamides followed by reduction. 14b,21 To assess the feasibility of the designed regioselective hydrofluorination of alkynes, readily accessible N-methyl-N-(3phenylprop-2-yn-1-yl)cyclohexanamine (1a) 22 were chosen as the model substrates. First, Et 3 N•3HF and 40% aqueous HF were tested as sources of HF using JohnPhosAuNTf 2 as the catalyst in toluene at 50 °C.…”