36388-09-7Relevant academic research and scientific papers
Platinum-Catalyzed, Terminal-Selective C(sp3)-H Oxidation of Aliphatic Amines
Lee, Melissa,Sanford, Melanie S.
supporting information, p. 12796 - 12799 (2015/10/28)
This Communication describes the terminal-selective, Pt-catalyzed C(sp3)-H oxidation of aliphatic amines without the requirement for directing groups. CuCl2 is employed as a stoichiometric oxidant, and the reactions proceed in high yield at Pt loadings as low as 1 mol%. These transformations are conducted in the presence of sulfuric acid, which reacts with the amine substrates in situ to form ammonium salts. We propose that protonation of the amine serves at least three important roles: (i) it renders the substrates soluble in the aqueous reaction medium; (ii) it limits binding of the amine nitrogen to Pt or Cu; and (iii) it electronically deactivates the C-H bonds proximal to the nitrogen center. We demonstrate that this strategy is effective for the terminal-selective C(sp3)-H oxidation of a variety of primary, secondary, and tertiary amines.
Hydrophobic amplification of noncovalent organocatalysis
Kleiner, Christian M.,Schreiner, Peter R.
, p. 4315 - 4317 (2007/10/03)
The effects of hydrogen-bonding organocatalysts and water for the acceleration of epoxide openings with a variety of nucleophiles are additive and lead to excellent yields of the catalyzed reactions in water. The Royal Society of Chemistry 2006.
Effect of branching in alkylgroups of tertiary amines on their performance as catalysts in the high pressure promoted Bylis-Hillman reaction
Schuurman,Linden,Grimbergen,Nolte,Scheeren
, p. 8307 - 8314 (2007/10/03)
Receptors 1 were tested as catalysts for the high pressure promoted Baylis-Hillman reaction. Surprisingly most of the compounds were found to be catalytically inactive. With model compounds (simple acyclic tertiary amines) it could be shown that tertiary amines with branches at their α-carbon atoms show a remarkable decreased activity. It is proposed that the branches prevent attack of the lone pair of the amine on the double bond of the alkene. This explains why only receptors without this feature are catalytically active.
