40326-16-7

Upstream product

• 558-30-5 2-methyl-1,2-epoxypropane 
• 7677-24-9 trimethylsilyl cyanide 
• 13435-20-6 tetraethylammoniumcyanide 
• 128816-20-6 Trifluoro-methanesulfonate1-(2-methyl-1-trimethylsilanyloxy-propyl)-pyridinium; 
• 142821-21-4 Trifluoro-methanesulfonate(2-methyl-1-trimethylsilanyloxy-propyl)-triphenyl-phosphonium; 
• 16966-40-8 isoselenocyanatotrimethylsilane 
• 78-84-2 isobutyraldehyde 

Downstream Products

• 15344-34-0 2-hydroxy-3-methylbutanenitrile 
• 161967-83-5 (R)-3-methyl-2-phenylbutanenitrile 

Relevant academic research and scientific papers

An uncoordinated tertiary nitrogen based tricarboxylate calcium network with Lewis acid-base dual catalytic sites for cyanosilylation of aldehydes

The design and utilization of dual sites for synergistic catalysts has been recognised as an efficient method towards high-efficiency catalysis in the cyanosilylation of aldehydes, which gives key intermediates for the synthesis of a number of valuable na

Enantioselective Synthesis of α-Thiocarboxylic Acids by Nitrilase Biocatalysed Dynamic Kinetic Resolution of α-Thionitriles

The enantioselective synthesis of α-thiocarboxylic acids by biocatalytic dynamic kinetic resolution (DKR) of nitrile precursors exploiting nitrilase enzymes is described. A panel of 35 nitrilase biocatalysts were screened and enzymes Nit27 and Nit34 were found to catalyse the DKR of racemic α-thionitriles under mild conditions, affording the corresponding carboxylic acids with high conversions and good-to-excellent ee. The ammonia produced in situ during the biocatalytic transformation favours the racemization of the nitrile enantiomers and, in turn, the DKR without the need of any external additive base.

Cyanosilylation of aldehydes catalyzed by a porous metal-organic framework containing a coordinatively unsaturated Zn(II) center and its anticancer activity in human osteogenic sarcoma

Solvothermal reaction of Zn(NO3) · 6H2O with the tripodal ligand 1,3,5-tris(4-carboxyphenyl)benzene (H3BTB) afforded a highly porous metal-organic framework (MOF) {[Zn3(BTB)2(H2O)2/su

Metal free mild and selective aldehyde cyanosilylation by a neutral penta-coordinate silicon compound

This study demonstrates the preparation and structural characterization of a Si(iv) hydride (PhC(NtBu)2SiH(CH3)Cl) (1) and its use as a catalyst for the cyanosilylation of a variety of aldehydes. Compound 1 represents the first neutr

A cationic aluminium complex: An efficient mononuclear main-group catalyst for the cyanosilylation of carbonyl compounds

A structurally characterized cationic aluminium complex [(AT)Al(DMAP)]+[OTf]- (3) stabilized through a relatively nonbulky aminotroponate (AT) ligand is reported (DMAP = 4-(dimethylamino)pyridine). This compound was found to work as

General and Stereocontrolled Approach to the Chemical Synthesis of Naturally Occurring Cyanogenic Glucosides

An effective method for the chemical synthesis of cyanogenic glucosides has been developed as demonstrated by the synthesis of dhurrin, taxiphyllin, prunasin, sambunigrin, heterodendrin, and epiheterodendrin. O-Trimethylsilylated cyanohydrins were prepared and subjected directly to glucosylation using a fully acetylated glucopyranosyl fluoride donor with boron trifluoride-diethyl etherate as promoter to afford a chromatographically separable epimeric mixture of the corresponding acetylated cyanogenic glucosides. The isolated epimers were deprotected using a triflic acid/MeOH/ion-exchange resin system without any epimerization of the cyanohydrin function. The method is stereocontrolled and provides an efficient approach to chemical synthesis of other naturally occurring cyanogenic glucosides including those with a more complex aglycone structure.

Insight into the catalytic properties and applications of metal-organic frameworks in the cyanosilylation of aldehydes

Here we present a systematic investigation of the cyanosilylation of aldehydes with trimethylsilyl cyanide (TMSCN) by using metal-organic frameworks (MOFs) as catalysts. Four types of thermally stable MOFs (MIL-47 (V), MIL-53 (Al), MIL-101 (Cr), and UiO-6

Catalytic asymmetric synthesis of secondary nitriles via stereoconvergent negishi arylations and alkenylations of racemic α-bromonitriles

The first method for the stereoconvergent cross-coupling of racemic α-halonitriles is described, specifically, nickel-catalyzed Negishi arylations and alkenylations that furnish an array of enantioenriched α-arylnitriles and allylic nitriles, respectively. Noteworthy features of this investigation include: the highly enantioselective synthesis of α-alkyl-α-aryl nitriles that bear secondary α-alkyl substituents; the first examples of the use of alkenylzinc reagents in stereoconvergent Negishi reactions of alkyl electrophiles; demonstration of the utility of a new family of ligands for asymmetric Negishi cross-couplings (a bidentate bis(oxazoline), rather than a tridentate pybox); in the case of arylzinc reagents, carbon-carbon bond formation at a remarkably low temperature (-78 °C), the lowest reported to date for an enantioselective cross-coupling of an alkyl electrophile; a mechanistic dichotomy between Negishi reactions of an unactivated versus an activated secondary alkyl bromide.

Perfectly green organocatalysis: Quaternary ammonium base triggered cyanosilylation of aldehydes

Quaternary ammonium bases, such as aqueous (CH3)4NOH, were found to be an extraordinarily efficient catalyst for cyanosilylation of aldehydes. The addition reaction of trimethylsilyl cyanide (TMSCN) to equivalent aldehydes could proceed smoothly with turnover frequency (TOF) up to 3000000 h-1 and in near 100% yield under solvent-free conditions. These organic catalysts also tolerated various aldehydes including aromatic, aliphatic and α,β-unsaturated aldehydes. This process perfectly conforms to the features of green chemistry: no waste regarding side-products and unconverted reactants, solvent-free, excellent catalytic activity, and no requirement for separation.

A dream combination for catalysis: Highly reactive and recyclable scandium(iii) triflate-catalyzed cyanosilylations of carbonyl compounds in an ionic liquid

The catalytic activity of lanthanide triflates, particularly scandium triflate, increased dramatically in [bmim][SbF6], allowing the cyanosilylation of a variety of aldehydes and ketones with a turnover frequency up to 48000 mol h-1 and a total turnover number of 100000.