A Commercially Available and User‐Friendly Catalyst for Hydroamination Reactions under Technical Conditions

Abstract

The activity of a simple, commercially available copper salt, [Cu(NCMe)4](BF4) in intramolecular hydroamination reactions of alkynes and allenes is presented. Reactions were successfully carried out in technical acetonitrile in the presence of air. While attempts of alkene hydroamination failed, this catalyst was also found active in intermolecular aza‐Michael reactions.

In Water Markovnikov Hydration and One‐Pot Reductive Hydroamination of Terminal Alkynes under Ruthenium Nanoparticle Catalysis

“…A primary amine present in solution might intercept the intermediate ketones obtained by Ru catalyzed hydration, and the imine formed reduced by the same Ru catalyst in the presence of a hydrogen donor. Several examples of alkyne hydroamination catalyzed by transition metal catalysts have been described to give the corresponding imine or enamine, [34][35][36][37] while few hydroamination procedures for the one-pot transformation of alkynes into secondary amine are known. [38,39] The reductive amination of acetophenone was firstly investigated on the crude separated after Ru-catalyzed hydration of phenylacetylene.…”

Copper‐catalyzed Regioselective Hydroaminations of Allylic Sulfones With Aromatic Amines

“…Among various catalysts that promote direct intermolecular addition reactions of arylamines to alkenes, copper, which is readily available, relatively inexpensive, and easy‐to‐handle, is a promising candidate for efficient and practical amination reactions. In the past decade, copper‐based catalysts have been used to improve reactivity and regio‐, chemo‐, and stereo‐control under mild reaction conditions 4 . For example, the Cu‐catalyzed intermolecular additions of anilines to highly activated α,β‐unsaturated carbonyl compounds with copper(II) triflate as the Lewis acid catalyst have been reported by Yamazaki and coworkers 5 .…”