92850-03-8Relevant articles and documents
Direct measurement of the thermodynamics of vinylarene hydroamination
Johns, Adam M.,Sakai, Norio,Ridder, Andre,Hartwig, John F.
, p. 9306 - 9307 (2006)
The thermodynamics for intermolecular hydroamination of vinylarenes with arylamines have been measured directly by conducting the addition processes, as well as cleavage of the addition products, under conditions in which amine, vinylarene, and phenethylamine are all present. The reaction of N-methylaniline with styrene is exothermic by about 10 kcal/mol but nearly thermoneutral in free energy. The free energies for additions of various primary arylamines to styrene and for additions of primary arylamines to indene, dihydronaphthalene, and two vinylarenes range from 1.3 to -3.5 kcal/mol (K = 0.16-155 M-1). The steric properties of the nucleophile significantly influenced the equilibrium constant for addition, but the electronic properties of the nucleophile had a minor effect on this equilibrium constant. These measurements have led to the first successful intermolecular addition of aniline to indene and 1,2-dihydronaphthalene and shed light on factors requiring consideration when choosing substrates and reaction conditions for this transformation. Copyright
Copper-catalyzed reductive amination of aromatic and aliphatic ketones with anilines using environmental-friendly molecular hydrogen
Werkmeister, Svenja,Junge, Kathrin,Beller, Matthias
supporting information, p. 2371 - 2374 (2013/02/21)
A convenient and practical copper-catalyzed reductive amination was discovered. In the presence of easily available and inexpensive Cu(OAc) 2 various ketones react with anilines and molecular hydrogen to give the desired amines in high yields.
