18840-23-8

Upstream product

• 775-12-2 diphenylsilane 
• 100-46-9 benzylamine 
• 98-88-4 benzoyl chloride 
• 2553-19-7 diethoxydiphenylsilane 
• 80-10-4 diphenylsilyl dichloride 

Relevant academic research and scientific papers

Diphenylsilane as a coupling reagent for amide bond formation

A simple procedure for amide bond formation using diphenylsilane as a coupling reagent is described. This methodology enables the direct coupling of carboxylic acids with primary and secondary amines, releasing only hydrogen and a siloxane as by-products. Only one equivalent of each partner is needed, providing a more sustainable amidation method producing minimal wastes. This methodology was also extended to the synthesis of peptides and lactams by addition of Hünig's base (DIPEA) and 4-dimethylaminopyridine (DMAP).

Alkaline-Earth-Catalysed Cross-Dehydrocoupling of Amines and Hydrosilanes: Reactivity Trends, Scope and Mechanism

Alkaline-earth (Ae=Ca, Sr, Ba) complexes are shown to catalyse the chemoselective cross-dehydrocoupling (CDC) of amines and hydrosilanes. Key trends were delineated in the benchmark couplings of Ph3SiH with pyrrolidine or tBuNH2. Ae{

Barium-Mediated Cross-Dehydrocoupling of Hydrosilanes with Amines: A Theoretical and Experimental Approach

Alkaline-earth (most prominently barium) complexes of the type [Ae{N(SiMe3)2}2(THF)x] and [{N^N}Ae{N(SiMe3)2}(THF)x] are very active and productive precatalysts (TON=396, TOF up

Hetero-dehydrocoupling of silanes and amines by heavier alkaline earth catalysis

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

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