39086-39-0

Upstream product

• 64-18-6 formic acid 
• 579-66-8 2,6-diethylaniline 
• 109-94-4 formic acid ethyl ester 
• 124-38-9 carbon dioxide 

Downstream Products

• 104310-90-9 (2,6-Diethyl-phenyl)-phosphoramidic acid diethyl ester 
• 1010456-81-1 3-(2,6-diethylphenyl)-4,5-dimethylthiazolium chloride 
• 2980-92-9 2,6-diethylphenyl isocyanide 

Relevant academic research and scientific papers

Access to Unsymmetrically Substituted Diaryl Gold N-Acyclic Carbene (NAC) and N-Heterocyclic Carbene (NHC) Complexes via the Isonitrile Route

A variety of unsymmetric diaryl gold N-acyclic carbene (NAC) complexes was synthesized via the isonitrile route by three different methods: (a) solvent free in a melt, (b) mechanochemically and (c) in THF at room temperature. The latter method can also be used to synthesize unsaturated gold NHC complexes. These methods overall offer access to a broad array of new complexes and remove one of the previous limitations of the isonitrile route to NAC and NHC complexes of gold, namely the inability to react with the less nucleophilic aromatic amines. The new complexes also proved to be successful as pre-catalysts in the gold-catalyzed phenol synthesis. (Figure presented.).

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.

Amine modified mesoporous Al2O3@MCM-41: An efficient, synergetic and recyclable catalyst for the formylation of amines using carbon dioxide and DMAB under mild reaction conditions

This work reports an amine modified meso Al2O3@MCM-41, particularly the ordered mesoporous silica, as a catalyst for the formylation of amines with carbon dioxide (CO2) and with dimethylamine-borane (DMAB) as a green reducing source. This newly developed catalytic system represents a heterogeneous and environmentally benign protocol. Besides this, the catalyst could be reused for five consecutive cycles without any significant loss in its catalytic activity towards the synthesis of formamides. The amine modified meso Al2O3@MCM-41 catalysts were well characterized by high and low angle XRD, temperature programmed desorption (TPD), BET-surface area, TGA/DTA and FT-IR analysis techniques. The effect of various reaction parameters such as temperature, CO2 pressure, time and the ratio of substrates to DMAB for the synthesis of formamides has been investigated. The developed protocol can be applicable for the synthesis of most important key intermediates like formoterol, orlistat, leucovarin and iguratimod in biologically active compounds.

Palladium-catalyzed cascade process consisting of isocyanide insertion and benzylic C(sp3)-H activation: Concise synthesis of indole derivatives

Synthesis of the indole skeleton was achieved using a Pd-catalyzed cascade process consisting of isocyanide insertion and benzylic C(sp3)-H activation. It was found that slow addition of isocyanide is effective for reducing the amount of catalyst needed and Ad2PnBu is a good ligand for C(sp3)-H activation. The construction of the tetracyclic carbazole skeleton was also achieved by a Pd-catalyzed domino reaction incorporating alkyne insertion.

A short way to switchable carbenes

A new, one-step route to N-heterocyclic oxo-carbene complexes (NHOCs), representatives of chemo-switchable NHC complexes, is reported. This simple procedure provides an easy access to gold, palladium and platinum complexes of these ligands. Copyright

Synthesis and activity of ruthenium olefin metathesis catalysts coordinated with thiazol-2-ylidene ligands

A new family of ruthenium-based olefin metathesis catalysts bearing a series of thiazole-2-ylidene ligands has been prepared. These complexes are readily accessible in one step from commercially available (PCy 3)2Cl2Ru=CHPh or (PCy3)Cl 2Ru=CH(o-iPrO-Ph) and have been fully characterized. The X-ray crystal structures of four of these complexes are disclosed. In the solid state, the aryl substituents of the thiazole-2-ylidene ligands are located above the empty coordination site of the ruthenium center. Despite the decreased steric bulk of their ligands, all of the complexes reported herein efficiently promote benchmark olefin metathesis reactions such as the ring-closing of diethyldiallyl and diethylallylmethallyl malonate and the ring-opening metathesis polymerization of 1,5-cyclooctadiene and norbornene, as well as the cross metathesis of allyl benzene with cis-1,4-diacetoxy-2-butene and the macrocyclic ring-closing of a 14-membered lactone. The phosphine-free catalysts of this family are more stable than their phosphine-containing counterparts, exhibiting pseudo-first-order kinetics in the ring-closing of diethyldiallyl malonate. Upon removing the steric bulk from the ortho positions of the N-aryl group of the thiazole-2-ylidene ligands, the phosphine-free catalysts lose stability, but when the substituents become too bulky the resulting catalysts show prolonged induction periods. Among five thiazole-2-ylidene ligands examined, 3-(2,4,6-trimethylphenyl)-and 3-(2,6-diethylphenyl)-4,5-dimethylthiazol-2- ylidene afforded the most efficient and stable catalysts. In the cross metathesis reaction of allyl benzene with cis-1,4-diacetoxy-2-butene increasing the steric bulk at the ortho positions of the N-aryl substituents results in catalysts that are more Z-selective.

Occurrence of alachlor environmental degradation products in groundwater

Groundwater samples collected beneath a Massachusetts corn field were analyzed by gas chromatography/mass spectrometry. In addition to alachlor, 20 compounds were detected whose EI and CIMS data indicated that they were derived from alachlor, presumably via environmental degradation. Structural assignments were confirmed for six of these compounds by analysis of standards. They were among 10 alachlor-related compounds that were synthesized by use of either the parent compound or 2,6-diethylaniline as starting material. -from Authors