4441-30-9Relevant 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.
HYDROBORATION D'AMINES ALLYLIQUES. REACTIVITE DES ORGANOBORANES
Baboulene, Michel,Torregrosa, Jean-Luc,Speziale, Vincent,Lattes, Armand
, p. 565 - 570 (2007/10/02)
Hydroboration of differently substituted allylic amines has been studied systematically.It was possible to demonstrate the importance of the hydroboration agent on the formation of aminoboranes.Oxidation of aminoboranes by hydrogen peroxyde in basic medium has ben examined and has led, with good yields, to primary aminoalcohols or a mixture of isomeric aminoalcohols.The influence of steric hindrance on the double bond and that of substitution of the nitrogen atom have been shown.
