Copper-catalysed selective hydroamination reactions of alkynes

The development of selective reactions that utilize easily available and abundant precursors for the efficient synthesis of amines is a long-standing goal of chemical research. Despite the centrality of amines in a number of important research areas, including medicinal chemistry, total synthesis and materials science, a general, selective and step-efficient synthesis of amines is still needed. Here, we describe a set of mild catalytic conditions utilizing a single copper-based catalyst that enables the direct preparation of three distinct and important amine classes (enamines, α-chiral branched alkylamines and linear alkylamines) from readily available alkyne starting materials with high levels of chemo-, regio- and stereoselectivity. This methodology was applied to the asymmetric synthesis of ​rivastigmine and the formal synthesis of several other pharmaceutical agents, including ​duloxetine, ​atomoxetine, ​fluoxetine and ​tolterodine.National Institutes of Health (U.S.) (GM58160

Expanding the Oxidative Chemistry of Organocopper Reagents: Facile Oxidative Cross-Coupling of Copper Acetylides with Arylboronic Acids

We have developed an efficient procedure for oxidative cross-coupling between arylboronic acids and alkynylcopper reagents. Upon simple addition of 1,10-phenanthroline in the presence of oxygen, these highly stable, readily available polymeric reagents are easily activated and transfer their alkynyl group after subsequent transmetallation with the boronic acid. These results further expand the oxidative chemistry of organocopper compounds together with providing a user-friendly entry to diaryl acetylenes.SCOPUS: ar.jinfo:eu-repo/semantics/publishe