142350-72-9Relevant academic research and scientific papers
Boron-Catalyzed Silylative Reduction of Nitriles in Accessing Primary Amines and Imines
Gandhamsetty, Narasimhulu,Jeong, Jinseong,Park, Juhyeon,Park, Sehoon,Chang, Sukbok
, p. 7281 - 7287 (2015/07/28)
Silylative reduction of nitriles was studied under transition metal-free conditions by using B(C6F5)3 as a catalyst with hydrosilanes as a reductant. Alkyl and (hetero)aryl nitriles were efficiently converted to primary amines or imines under mild conditions. The choice of silanes was found to determine the selectivity: while a full reduction of nitriles was highly facile, the use of sterically bulky silanes allowed for the partial reduction leading to N-silylimines.
Hetero-dehydrocoupling of silanes and amines by heavier alkaline earth catalysis
Hill, Michael S.,Liptrot, David J.,Macdougall, Dugald J.,Mahon, Mary F.,Robinson, Thomas P.
, p. 4212 - 4222 (2013/10/22)
The homoleptic alkaline earth hexamethyldisilazides, [M{N(SiMe 3)2}2]2 (1: M = Mg; 2: M = Ca; 3: M = Sr), have been demonstrated as active pre-catalysts for the cross-dehydrocoupling of Si-H and N-H bonds under mild (25-60 °C) conditions. The reactions are applicable to the coupling of a wide variety of amine and silane substrates and are proposed to occur via a sequence of discrete Si-H/M-N and N-H/M-H metathesis steps. Whereas reactions of dialkyl group 2 species with 2,6-di-iso-propylaniline and phenylsilane delivered a series of well-defined compounds consistent with this rationale, kinetic analysis of the cross-coupling of diethylamine with diphenylsilane provided evidence for a more complex and subtly variable mechanistic landscape. Although reactions performed with all three pre-catalysts presented a number of common features, in every case the calcium species, 2, was found to provide notably superior catalytic activity, an order of magnitude higher than both 1 and 3 and in excess of many previously described benchmark transition metal- or f-element-mediated processes. Variations in overall reaction order, mode of pre-catalyst activation and the nature of the rate determining process are postulated to arise as a consequence of the marked change in M2+ radius and resultant charge density as group 2 is descended. The Royal Society of Chemistry 2013.
Copper(I)-catalyzed cross-dehydrocoupling reactions of silanes and amines
Liu, H. Q.,Harrod, J. F.
, p. 107 - 110 (2007/10/02)
In the presence of cuprous chloride, hydrosilanes and primary amines react to give silazanes.Methylphenylsilane reacts with (R)-(+)-α-methylbenzylamine to give the two diastereomeric monosilazanes as the only products.Aniline and benzylamine react with me
