1373393-10-2

Upstream product

• 623-27-8 terephthalaldehyde, 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 16721-03-2 1,4-bis-benzyloxymethyl-benzene 

Downstream Products

• 589-29-7 p-xylylene glycol 

Relevant academic research and scientific papers

N-Heterocyclic Carbene-Phosphinidenide Complexes as Hydroboration Catalysts

The reactions of the N-heterocyclic carbene-phosphinidene adducts (NHC)PSiMe3 and (NHC)PH with the dinuclear ruthenium and osmium complexes [(η6-p-cymene)MCl2]2 (M = Ru, Os) afforded the half-sandwich complexes

An Unsymmetric Imino-Phosphanamidinate Ligand and its Y(III) Complex: Synthesis, Characterization, and Catalytic Hydroboration of Carbonyl Compounds

An imino-phosphanamide ligand, [NHIiPr2Me2P(Ph)NH-2,6-iPr2C6H3] (LH), containing two different N-substituents was prepared by the direct reaction of the lithium salt of N-heterocyclic imine (NHI) with phenylchloro-2,6-diisopropylphenyl phosphanamine, PhP(

Ruthenium-catalyzed selective hydroboronolysis of ethers

A ruthenium-catalyzed reaction of HBpin with substituted organic ethers leads to the activation of C?O bonds, resulting in the formation of alkanes and boronate esters via hydroboronolysis. A ruthenium precatalyst, [Ru (p-cymene)Cl]2Cl2 (1), is employed, and the reactions proceed under neat conditions at 135 °C and atmospheric pressure (ca. 1.5 bar at 135 °C). Unsymmetrical dibenzyl ethers undergo selective hydroboronolysis on relatively electron-poor C?O bonds. In arylbenzyl or alkylbenzyl ethers, C?O bond cleavage occurs selectively on CBn?OR bonds (Bn = benzyl); in alkylmethyl ethers, selective deconstruction of CMe?OR bonds leads to the formation of alkylboronate esters and methane. Cyclic ethers are also amenable to catalytic hydroboronolysis. Mechanistic studies indicated the immediate in situ formation of a mono-hydridobridged dinuclear ruthenium complex [{(η6-p-cymene)RuCl}2(μ?H?μ?Cl)] (2), which is highly active for hydroboronolysis of ethers. Over time, the dinuclear species decompose to produce ruthenium nanoparticles that are also active for this transformation. Using this catalytic system, hydroboronolysis could be applied effectively to a very large scope of ethers, demonstrating its great potential to cleave C?O bonds in ethers as an alternative to traditional hydrogenolysis.

Practical and selective hydroboration of aldehydes and ketones in air catalysed by an iron(ii) coordination polymer

The in air catalytic hydroboration of ketones and aldehydes with pinacolborane by an iron(ii) coordination polymer (CP) is carried out under mild and solvent-free conditions. The precatalyst is highly active towards a wide range of substrates including functionalized ketones and aldehydes in the presence of KOtBu as an activator, achieving a high turnover number (TON) of up to 9500. Excellent chemoselectivity to aldehydes over ketones was also revealed, which is in sharp contrast with the results obtained under inert atmosphere using the same catalyst system. This catalyst observed here is not only highly efficient but also recyclable for reuse for at least 5 times without losing its effectiveness.

Structure-property-reactivity studies on dithiaphospholes

The reaction of either toluene-3,4-dithiol or benzene dithiol with phosphorus(iii) trihalides generates the corresponding benzo-fused 1,3,2-dithiaphospholes, RC6H3S2PX (R = Me (1), R = H (2); X = Cl, Br, I). The P-chloro-dithiaphospholes undergo: (a) halogen abstraction reactions with Lewis acids forming phosphenium cations; (b) substitution with LiHMDS base and; (c) reduction chemistry with sodium metal to generate the P-P σ-bonded dimer, (RC6H3S2P)2. Reduction catalysis of aldehydes with pinacolborane using dithiaphospholes is compared with their dioxaphosphole and diazaphosphole counterparts as pre-catalysts, revealing interesting differences in the reactivity of this series of compounds.

Efficient and Selective Iron-Complex-Catalyzed Hydroboration of Aldehydes

An imine-coupled [Fe-N2S2]2 complex, prepared from a readily available benzothiazolidine ligand, catalyzes selectively the hydroboration of aliphatic and aromatic aldehydes at low catalyst loadings (0.1 mol %) using pinaco

Arsenic Catalysis: Hydroboration of Aldehydes Using a Benzo-Fused Diaza-benzyloxy-arsole

The first example of a homogenous AsIII catalyst for hydroboration has been established. The reaction of N,N′-diisopropylbenzene diamine or toluene-3,4-dithiol with AsCl3 yielded the chloroarsoles (1 and 2), which upon reaction with

Electrostatic Catalyst Generated from Diazadiborinine for Carbonyl Reduction

Since the seminal discovery by van der Waals in the late 19th century that weak attractive forces exist between even electrically neutral atoms or molecules, a number of noncovalent interactions have been recognized. Among them, electrostatic interactions such as hydrogen bonds play pivotal roles in countless chemical processes and biochemical living systems. By mimicking biocatalysis, various organocatalysts equipped with hydrogen-bond functionality have been developed; however, a challenge has persisted in designing catalysts exploiting other types of noncovalent interactions. Here, we report metal-free hydroboration reactions of carbonyl compounds and CO2 catalyzed by aromatic diazadiborinine. A joint experimental and computational study on the reaction mechanism suggests that adducts of diazadiborinine with carbonyl and CO2 formed at the initial stage of the reactions serve as actual catalysts. The former stabilizes the transition state by using the electrostatic interaction between the hydride of borane and the polar, hole-shaped structure of the adduct.

Catalytic hydroboration of aldehydes, ketones, alkynes and alkenes initiated by NaOH

Commercially available NaOH powder is shown to be an efficient transition-metal-free initiator for the catalytic hydroboration of aldehydes, ketones, alkynes and alkenes with HBpin and 9-BBN under mild conditions. Combined experimental and theoretical stu

Main group metal-ligand cooperation of N-heterocyclic germylene: An efficient catalyst for hydroboration of carbonyl compounds

N-heterocyclic ylide-like germylene effectively promotes the hydroboration of aldehydes and ketones under mild conditions with broad substrate tolerance, operational simplicity of procedure and excellent yields. A key intermediate in this catalytic system