1265032-57-2

Upstream product

• 775-12-2 diphenylsilane 
• 100-10-7 4-dimethylamino-benzaldehyde 

Downstream Products

• 1703-46-4 N,N-dimethyl-4-hydroxymethylaniline 

Relevant academic research and scientific papers

Efficient hydrosilylation of carbonyl compounds with the simple amide catalyst [Fe{N(SiMe3)2}2]

Keep it simple: A variety of ketones and two aldehydes underwent efficient hydrosilylation under mild conditions in the presence of the title complex (see scheme; R,R′=H, alkyl, aryl). In some cases, a catalyst loading of just 0.01-0.03 mol % was sufficie

Hydrosilylation of Carbonyl Compounds Catalyzed by a Nickel Complex Bearing a PBP Ligand

The efficient catalytic hydrosilylation of ketones and aldehydes has been investigated using a nickel pincer hydride complex supported by a diphosphino-boryl ligand (PBP). It was found that the presence of the boryl group within the skeleton of the ligand has a beneficial effect on the catalytic activities observed for ketones compared to related pincer systems. The analysis of the reaction mechanism allows for the synthesis and characterization of a nickel alkoxide derivative by insertion of the carbonyl moiety into the Ni?H bond. Combined experimental and theoretical analysis (DFT) support a reaction mechanism that involves the initial formation of an alkoxide complex followed by reaction with the silane to release the corresponding silyl ether and regenerate the catalyst.

E-H Bond Activations and Hydrosilylation Catalysis with Iron and Cobalt Metalloboranes

An exciting challenge in transition metal catalyst design is to explore whether earth-abundant base metals such as Fe, Co, and Ni can mediate two-electron reductive transformations that their precious metal counterparts (e.g., Ru, Rh, Ir, and Pd) are better known to catalyze. Organometallic metalloboranes are an interesting design concept in this regard because they can serve as organometallic frustrated Lewis pairs. To build on prior studies with nickel metalloboranes featuring the DPB and PhDPBMes ligands in the context of H2 and silane activation and catalysis (DPB = bis(o-diisopropylphosphinophenyl)phenylborane, PhDPBMes = bis(o-diphenylphosphinophenyl)mesitylborane), we now explore the reactivity of iron, [(DPB)Fe]2(N2), 1, and cobalt, (DPB)Co(N2), 2, metalloboranes toward a series of substrates with E-H bonds (E = O, S, C, N) including phenol, thiophenol, benzo[h]quinoline, and 8-aminoquinoline. In addition to displaying high stoichiometric E-H bond activation reactivity, complexes 1 and 2 prove to be more active catalysts for the hydrosilylation of ketones and aldehydes with diphenylsilane relative to (PhDPBMes)Ni. Indeed, 2 appears to be the most active homogeneous cobalt catalyst reported to date for the hydrosilylation of acetophenone under the conditions studied.

Iron-Catalyzed Hydrosilylation of Aldehydes and Ketones under Solvent-Free Conditions

Exposure of aldehyde or ketone to 1 mol % BIAN-Fe(C7H8) complex in the presence of diphenyl silane affords the corresponding protected alcohol in excellent yields, under mild reaction conditions. Aldehydes and ketones are reduced cleanly in the presence of a broad range of functional groups under solvent-free conditions.

Facile Si-H bond activation and hydrosilylation catalysis mediated by a nickel-borane complex

Metal-borane complexes are emerging as promising systems for study in the context of bifunctional catalysis. Herein we describe diphosphineborane nickel complexes that activate Si-H bonds and catalyze the hydrosilylation of aldehydes. Treatment of [MesDPBPh]Ni (1) ([ MesDPBPh] = MesB(o-Ph2PC6H 4)2) with organosilanes affords the complexes [ MesDPBPh](μ-H)NiE (E = SiH2Ph (3), SiHPh2 (4)). Complex 4 is in solution equilibrium with 1 and the thermodynamic and kinetic parameters of their exchange have been characterized by NMR spectroscopy. Complex 1 is a catalyst for the hydrosilylation of a range of para-substituted benzaldehydes. Mechanistic studies on this reaction via multinuclear NMR spectroscopy are consistent with the intermediacy of a borohydrido-Ni-siloxyalkyl species.