74418-30-7Relevant academic research and scientific papers
Amine-boranes as Dual-Purpose Reagents for Direct Amidation of Carboxylic Acids
Choudhary, Shivani,Hamann, Henry J.,Ramachandran, P. Veeraraghavan
supporting information, (2020/11/13)
Amine-boranes serve as dual-purpose reagents for direct amidation, activating aliphatic and aromatic carboxylic acids and, subsequently, delivering amines to provide the corresponding amides in up to 99% yields. Delivery of gaseous or low-boiling amines as their borane complexes provides a major advantage over existing methodologies. Utilizing amine-boranes containing borane incompatible functionalities allows for the preparation of functionalized amides. An intermolecular mechanism proceeding through a triacyloxyborane-amine complex is proposed.
"spontaneous" ambient temperature dehydrocoupling of aromatic amine-boranes
Helten, Holger,Robertson, Alasdair P. M.,Staubitz, Anne,Vance, James R.,Haddow, Mairi F.,Manners, Ian
experimental part, p. 4665 - 4680 (2012/05/31)
The dehydrocoupling/dehydrogenation behavior of primary arylamine-borane adducts ArNH2·BH3 (3-a-c; Ar=a: Ph, b: p-MeOC 6H4, c: p-CF3C6H4) has been studied in detail both in solut
The kinetics and mechanism of solvolysis of amineboranes
Kelly, Henry C.,Marchelli, Frank R.,Giusto, Mario B.
, p. 431 - 437 (2008/10/08)
The rates of solvolysis of substituted phenylamineboranes in aqueous dioxane are described by the expression -d[AB]/dt/ = (k1 + k2[H+]) where [AB] = concentration of amineborane. The acid-independent solvolysis rate is accelerated and the acid-dependent rate retarded by electron-withdrawing para and meta ring substituents, by increasing N-alkyl substitution and by increasing dioxane content of the solvent. No primary hydrogen isotope effects were observed for either mode of solvolysis. For the acid-independent reaction, the rate of disappearance of amineborane equals the rate of appearance of free amine. This rate is not significantly influenced by the addition of moderate amounts of free amine or neutral salt and is essentially the same in dioxane-D2O as in dioxane-H2O. The acid-dependent rate is subject to general acid catalysis and k2 exhibits a slight positive salt effect. Mechanisms for both modes of solvolysis are proposed. Data for the hydrolysis of selected alkyl and heterocyclic amineboranes, including the effect of variations in structure on rate indicate that these substrates hydrolyze by a mechanism similar to that proposed for the acid-dependent solvolysis of arylamineboranes.
