4623-21-6

Usage

InChI:InChI=1/C24H21N3O6/c1-31-19-10-4-16(5-11-19)25-22(28)26(17-6-12-20(32-2)13-7-17)24(30)27(23(25)29)18-8-14-21(33-3)15-9-18/h4-15H,1-3H3

Upstream product

• 5416-93-3 4-Methoxyphenyl isocyanate 
• 16208-36-9 2-benz-(E)-ylidenehydrazinecarboxylic acid ethyl ester 

Relevant academic research and scientific papers

Synergistic Catalysis by Br?nsted Acid/Carbodicarbene Mimicking Frustrated Lewis Pair-Like Reactivity

Carbodicarbene (CDC), unique carbenic entities bearing two lone pairs of electrons are well-known for their strong Lewis basicity. We demonstrate herein, upon introducing a weak Br?nsted acid benzyl alcohol (BnOH) as a co-modulator, CDC is remolded into a Frustrated Lewis Pair (FLP)-like reactivity. DFT calculation and experimental evidence show BnOH loosely interacting with the binding pocket of CDC via H-bonding and π-π stacking. Four distinct reactions in nature were deployed to demonstrate the viability of proof-of-concept as synergistic FLP/Modulator (CDC/BnOH), demonstrating enhanced catalytic reactivity in cyclotrimerization of isocyanate, polymerization process for L-lactide (LA), methyl methacrylate (MMA) and dehydrosilylation of alcohols. Importantly, the catalytic reactivity of carbodicarbene is uniquely distinct from conventional NHC which relies on only single chemical feature of nucleophilicity. This finding also provides a new spin in diversifying FLP reactivity with co-modulator or co-catalyst.

Method for preparing aromatic isocyanate terpolymer

The invention discloses a method for preparing an aromatic isocyanate terpolymer in the field of high polymer material synthesis, which comprises the following steps of S1, respectively taking dimethylacetamide, ethanol and sodium hydride, taking dimethylacetamide as a solvent, taking ethanol and sodium hydride as catalysts, adding into a flask, and reacting at room temperature, S2, dropwise adding aromatic isocyanate as a reaction substrate, and carrying out a heating reaction under magnetic stirring, S3, after the mixture is cooled to the room temperature, pouring the mixture into ultrapure water to separate out a product, filtering the product, washing the precipitate with water and ethanol in sequence, and drying the precipitate in a drying oven to obtain a crude product. According to the method, dimethylacetamide is used as a solvent, under the condition that ethanol is not changed, a small amount of sodium hydride is used for base catalysis of polymerization of aromatic isocyanate such as 3, 5-dimethyl phenyl isocyanate to synthesize the compound aromatic isocyanate tripolymer, the yield of the aromatic isocyanate tripolymer can be increased, the cost can be reduced, and use by people is facilitated.

Fast cyclotrimerization of a wide range of isocyanates to isocyanurates over acid/base conjugates under bulk conditions

An array of organic bases DMAP (4-dimethylaminopyridine), DBU (1, 8-diazabicyclo [5.4.0] undec-7-ene), TBD (1, 5, 7-triazabicyclo [4.4.0] dec-5-ene), and their base/acid conjugate organocatalyst systems were evaluated in the trimerization of various isocyanates. The performance depended greatly on the combination of the catalyst systems, and the [HTBD][OAc] (acetic acid) catalyst systems were considerably the most active in contrast to the corresponding DMAP and DBU counterparts. The [HTBD][OAc] catalyst system was capable of providing isocyanurates from the cyclotrimerization of various isocyanate substrates in excellent yields in seconds even under bulk conditions. A bifunctional catalytic mechanism over [HTBD][OAc] was proposed.

Yttrium dialkyl supported by a silaamidinate ligand: Synthesis, structure and catalysis on cyclotrimerization of isocyanates

A sterically demanding silaamidine (ArN = Si(L)NHAr) ligand was synthesized and employed for the preparation of a yttrium dialkyl complex, which catalytically enabled the cyclotrimerization of isocyanate with high activity and excellent functional group t

Highly efficient cyclotrimerization of isocyanates using N-heterocyclic olefins under bulk conditions

With a catalyst loading as low as 0.005%, high to excellent yields of isocyanurates could be achieved from N-heterocyclic olefin mediated organocatalytic cyclotrimerization of a wide range of isocyanates under bulk conditions. Experimental details coupled with structural characterization of the key intermediates led to comprehensive mechanistic studies of cyclotrimerization.

Potassium complexes containing bidentate pyrrole ligands: Synthesis, structures, and catalytic activity for the cyclotrimerization of isocyanates

Bidentate pyrrolyl ligands, 2-(t-butyliminomethyl)pyrrole and 2-(t-butylaminomethyl)pyrrole, reacted with KH to give complexes [C4H3N(2-CHNtBu)K(THF)]n (1) and [C4H3N(2-CH2NHsup

Aluminium-catalysed isocyanate trimerization, enhanced by exploiting a dynamic coordination sphere

Main-group metals are inherently labile, hindering their use in catalysis. We exploit this lability in the synthesis of isocyanurates. For the first time we report a highly active catalyst that trimerizes alkyl, allyl and aryl isocyanates, and di-isocyanates, with low catalyst loadings under mild conditions, using a hemi-labile aluminium-pyridyl-bis(iminophenolate) complex.

Lithium complex of 2-amino-functionalized benzoylpyrrole: Synthesis, structure, and catalytic activity for the cyclotrimerization of isocyanates

Lithium complex stabilised by 2-amino-functionalized benzoylpyrrole was synthesized, and its structural features were provided. The molecular structure shows a novel tetrameric cage structure, which includes a eight-membered (LiN)4 ring and a e

Macrocyclic complexes containing a platinacycle or palladacycle composed of an isocyanate dimer unit: Reactivity towards isocyanides and cyclotrimerization of isocyanates

The reactions of [Pt(styrene)(PMe3)2] with 2 equiv. of alkyl or aryl isocyanate affored five-membered platinacycles, cis-[Pt{-N(R)C(O)N(R)C(O)-}(PMe3)2] (R = CH2C6H5, p-ClC6H4, p-OMeC6H4). These complexes are the first examples of platinacycles containing an isocyanate dimer unit. When the five-membered bis(phosphine) platinacycles or palladacycles were treated with 2 equiv. of elemental sulfur, 16-membered cyclic products as an assembly of four platinacycles or palladacycles, [M(PR3){-N(R)C(O)N(R)C(O)-}]4, were readily obtained. These cyclic tetramers were cleaved using tert-butyl isocyanide (CN-tbutyl, 4 equiv.), affording the corresponding monomeric complexes, [M(PR3)(CN-tbutyl){-N(R)C(O)N(R)C(O)-}] (M = Pt, Pd). An unusual cyclotrimerization of organic isocyanates catalyzed by zerovalent Pt complexes or five-membered platinacycles was observed. In addition, the direct cyclotrimerization of alkyl or aryl isocyanates using dialkyl Pt(II) or Pd(II) complexes was investigated. The cross cyclotrimerization of an aryl isocyanate and its derivative using a zerovalent Pd complex was also investigated.

Lithium, magnesium, zinc complexes supported by tridentate pincer type pyrrolyl ligands: Synthesis, crystal structures and catalytic activities for the cyclotrimerization of isocyanates

Lithium, magnesium, zinc complexes incorporating substituted symmetrical tridentate pyrrolyl ligands were synthesized conveniently and their application for the cyclotrimerization of isocyanate to corresponding isocyanurate has been investigated. The reac