17590-41-9

Upstream product

• 80-10-4 diphenylsilyl dichloride 
• 1000206-70-1 1,1,3,3-tetramethyl-2,2-diphenyl-1,2,3-trisilacyclohexane 
• 109-89-7 diethylamine 
• 775-12-2 diphenylsilane 

Downstream Products

• 17591-75-2 2,3,3,5-tetraphenyl-3,4-dihydro-2H-[1,2,4,3]triazasilole 

Relevant academic research and scientific papers

Syntheses of Dianionic α-Iminopyridine Rare-Earth Metal Complexes and Their Catalytic Acitivities toward Dehydrogenative Coupling of Amines with Hydrosilanes

Reactions of [(Me3Si)2N]3RE(μ-Cl)Li(THF)3 with aminomethylene-substituted pyridine 2-[O(CH2CH2)2NCH2CH2NCH2]C5H4N (1) gave the dianionic α-iminopyridine rare-earth metal amido complexes {μ-η2:σ1:κ1:κ1-2-[O(CH2CH2)2NCH2CH2NCH]C5H4N}2RE2[N(SiMe3)2]2 (RE = Y(2a), La(2b), Pr(2c), Nd(2d), Sm(2e), Dy(2f), Er(2g), and Lu (2h)). However, reaction of [(Me3Si)2N]3Y(μ-Cl)Li(THF)3 with pyridin-2-ylmethyl-substituted amines such as 2-(RNHCH2)C5H4N (R = tBu (3a) and 2,6-iPr2Ph (3b)) or benzyl-substituted amine O(CH2CH2)2NCH2CH2NHCH2C6H5 (5) afforded the corresponding yttrium complexes containing monoanionic ligands [2-(RNCH2)C5H4N]2YN(SiMe3)2 (R = tBu (4a) and 2,6-iPr2Ph (4b)) or [O(CH2CH2)2NCH2CH2NCH2C6H5][(Me3Si)2N)]Y(μ-Cl)(μ-η3-O(CH2CH2)2NCH2CH2NCH2C6H5)Li(THF) (6). Dianionic α-iminopyridine rare-earth metal amido complexes showed high catalytic activities for the dehydrogenation coupling reaction of hydrosilanes and amines providing a variety of silylamines in high yields.

Photoactivated silicon-oxygen and silicon-nitrogen heterodehydrocoupling with a commercially available iron compound

Silicon-oxygen and silicon-nitrogen heterodehydrocoupling catalyzed by the commercially available cyclopentadienyl dicarbonyl iron dimer [CpFe(CO)2]2 (1) under photochemical conditions is reported. Reactions between alcohols and PhSi

Selective catalytic synthesis of amino-silanes at part-per million catalyst loadings

Platinum(ii) complex [Pt(ItBu′)(ItBu)][BArF4] (1a) is a highly active and selective catalyst in the dehydrocoupling of amines and silanes at part-per-million catalyst loadings (up to 10 ppm, 0.001 mol%), achievi

Si-N Heterodehydrocoupling with a Lanthanide Compound

[La{N(SiMe3)2}3THF2] (1) is an effective precatalyst for the heterodehydrocoupling of silanes and amines. Coupling of primary and secondary amines with aryl silanes was achieved with a loading of 0.8 mol % of [L

Organomagnesium amide catalyzed cross-dehydrocoupling of organosilanes with amines

The synthesis of novel heteroleptic organomagnesium(ii) amide complexes [IMesMg(Ar){N(SiMe3)2}]; (IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene), Ar = 2,6-Me2C6H3 (Xyl) (1) and 2,4,6-Me

Alkali-Metal-Catalyzed Cross-Dehydrogenative Couplings of Hydrosilanes with Amines

We report the N-H/H-Si cross-dehydrogenative coupling (CDC) of hydrosilanes and amines with high conversion (>90 %) and chemoselectivity for the production of silazanes, using group 1 metal hexamethyldisilazides [MN(SiMe3)2] (M=Li, Na, K) as precatalysts under mild conditions. [KN(SiMe3)2] showed higher activity than the congeneric lithium and sodium salts. The catalyzed CDC reaction displays a broad substrate scope. Phenylsilane and diphenylsilane react with a number of amines under ambient conditions; more elevated temperature is required for triphenylsilane to undergo CDC reactions. The intermediate lithium complex [(THF)2Li-{N(SiHPh2)(Dipp)}] (1) has been isolated and characterized in an attempt to identify the operative reaction mechanism.

Homoleptic Divalent Dialkyl Lanthanide-Catalyzed Cross-Dehydrocoupling of Silanes and Amines

The rare-earth bis(alkyl) compound Sm{C(SiHMe2)3}2THF2 (1b) is prepared by the reaction of samarium(II) iodide and 2 equiv of KC(SiHMe2)3. This synthesis is similar to that of previously re

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.

[(NHC)Yb{N(SiMe3)2}2]-catalyzed cross-dehydrogenative coupling of silanes with amines

Top cat: [(NHC)Yb{N(SiMe3)2}2] adducts (NHC=N-heterocyclic carbene) are efficient catalysts for catalytic cross-dehydrogenative coupling of silanes with a range of primary and secondary amines to yield silylamines in high

Kinetics and mechanisms of the reactions of transient silylenes with amines

The N-H insertion reactions of dimethyl-, diphenyl-, and dimesitylsilylene (SiMe2, SiPh2, and SiMes2, respectively) with n-butylamine (BuNH2) and diethylamine (Et2NH) were studied in hexanes by steady-state and laser photolysis methods. The process begins with the formation of the corresponding Lewis acid-base complexes, which decayed with second-order kinetics at rates that show modest sensitivity to silylene and amine structures. The complexation process, which was also studied using triethylamine (Et3N), proceeds at rates close to the diffusion limit, but the rate constants vary systematically with steric bulk in the amine. Equilibrium constants were determined for the complexation of Et2NH and Et3N with SiMes2, which proceeds reversibly. The complexes of SiMe2 and SiPh2 with BuNH2 and Et2NH decayed with pseudo-first-order rate coefficients in the 104-105s-1 range. This is consistent with upper limits of about 106M-1s-1 for the rate constants for amine-catalyzed H-migration, which is thought to be the dominant mechanism for product formation from the complexes. The results are compared to published kinetic data for the O-H insertion reactions of these silylenes with alcohols, which also proceeds via initial complexation followed by catalytic proton transfer. The results indicate that catalyzed H-transfer in the amine complexes is at least 104 times slower than the analogous process in silylene-MeOH complexes. The experimental data are compared to the results of theoretical calculations of the SiMe2+NH2Me and SiMe 2+MeOH potential energy surfaces, carried out at the Gaussian-4 and B3LYP/6-311+G(d,p) levels of theory.