18109-39-2

Upstream product

• 98-88-4 benzoyl chloride 
• 87-62-7 2,6-dimethylaniline 
• 137-40-6 sodium proprionate 
• 2192-33-8 2,6-dimethylbenzenediazonium tetrafluoroborate 
• 100-47-0 benzonitrile 
• 33008-36-5 α-phenyl-N-(2,6-dimethylphenyl)nitrone 
• 7497-27-0 Trifluoracetyl-2',6'-dimethylanilid 
• 591-51-5 phenyllithium 
• 246872-23-1 N-{bis[3,5-bis(trifluoromethyl)phenyl]methylidene}(2,6-dimethylaniline) 
• 100-52-7 benzaldehyde 
• 108-86-1 bromobenzene 
• 119072-54-7 2,6-dimethylphenyl isonitrile 
• 108-88-3 toluene 
• 93-89-0 benzoic acid ethyl ester 

Downstream Products

• 59387-01-8 N-(2,6-dimethylphenyl)benzenecarboximidoyl chloride 
• 31684-74-9 (4-amino-3,5-dimethylphenyl)phenylmethanone 
• 872513-77-4 bis[N-2,6-dimethylphenyl(phenyl)amidato]dibenzylhafnium 
• 791811-42-2 N'-methoxy-N'-methyl-N-(2,6-dimethylphenyl)benzamidine 
• 16819-50-4 N-(2,6-dimethylphenyl)benzylamine 
• 3096-95-5 2,6-dimethyl-N-(benzylidene)aniline 
• 26060-29-7 Thiobenzoesaeure-<2,6-dimethyl-anilid> 
• 121732-47-6 2-benzoylamino-isophthalic acid 
• 111241-03-3 N-(2,6-dimethyl-phenyl)-benzimidic acid-(3-methyl-but-2-enyl ester) 

Relevant academic research and scientific papers

Synthesis, characterization, and reactivity of the first hafnium alkyl complex stabilized by amidate ligands

A photo and thermally stable bis(amidate)-dibenzyl complex of Hf ([ DMP(NO)Ph]2Hf(CH2Ph) 2(THF) (2a) was formed as a monosolvated THF adduct in near quantitative yield from Hf(CH2Ph)4

Buchwald-Hartwig cross-coupling of amides (transamidation) by selective N-C(O) cleavage mediated by air- And moisture-stable [Pd(NHC)(allyl)Cl] precatalysts: Catalyst evaluation and mechanism

The Pd-NHC-catalyzed acyl-type Buchwald-Hartwig cross-coupling of amides by N-C(O) cleavage (transamidation) provides a valuable alternative to the classical methods for amide synthesis. Herein, we report a combined experimental and computational study of the Buchwald-Hartwig cross-coupling of amides using well-defined, air- and moisture-stable [Pd(NHC)(allyl)Cl] precatalysts. Most crucially, we present a comprehensive evaluation of a series of distinct Pd(ii)-NHC precatalysts featuring different NHC scaffolds and throw-away ligands for the synthesis of functionalized amides that are not compatible with stoichiometric transition-metal-free transamidation methods. Furthermore, we present evaluation of the catalytic cycle by DFT methods for a series of different Pd(ii)-NHC precatalysts. The viability of accessing NHC-supported acyl-palladium(ii) amido complexes will have implications for the design and development of cross-coupling methods involving stable amide electrophiles.

Sterically hindered (pyridyl)benzamidine palladium(II) complexes: Syntheses, structural studies, and applications as catalysts in the methoxycarbonylation of olefins

Reactions of ligands (E)-N′-(2,6-diisopropylphenyl)-N-(4-methylpyridin-2-yl)benzimidamide (L1), (E)-N′-(2,6-diisopropylphenyl)-N-(6-methylpyridin-2-yl)benzimidamide (L2), (E)-N′-(2,6-dimethylphenyl)-N-(6-methylpyridin-2-yl)benzimidamide (L3), (E)-N′-(2,6-dimethylphenyl)-N-(4-methylpyridin-2-yl)benzimidamide (L4), and (E)-N-(6-methylpyridin-2-yl)-N′-phenylbenzimidamide (L5) with [Pd(NCMe)2Cl2] furnished the corresponding palladium(II) precatalysts (Pd1–Pd5), in good yields. Molecular structures of Pd2 and Pd3 revealed that the ligands coordinate in a N^N bidentate mode to afford square planar compounds. Activation of the palladium(II) complexes with para-tolyl sulfonic acid (PTSA) afforded active catalysts in the methoxycarbonylation of a number of alkene. The resultant catalytic activities were controlled by the both the complex structure and alkene substrate. While aliphatic substrates favored the formation of linear esters (>70%), styrene substrate resulted in the formation of predominantly branched esters of up to 91%.

N -Heterocyclic carbene (NHC) catalyzed amidation of aldehydes with amines via the tandem N -hydroxysuccinimide ester formation

A facile method for the amidation of aldehydes by a cascade approach was developed. This methodology, reported for the first time, uses a N-heterocyclic carbene (NHC) as the catalyst, and N-hydroxysuccinimide (NHS) mediated synthesis of amides utilising TBHP as the oxidant. Various substituted aldehydes reacted smoothly with NHS giving the corresponding active esters in moderate to good yields, which facilely converted into amides in one pot. In addition, the drug moclobemide was synthesized to represent the practical utility of the developed methodology. This journal is

Direct Amidation of Esters by Ball Milling**

The direct mechanochemical amidation of esters by ball milling is described. The operationally simple procedure requires an ester, an amine, and substoichiometric KOtBu and was used to prepare a large and diverse library of 78 amide structures with modest to excellent efficiency. Heteroaromatic and heterocyclic components are specifically shown to be amenable to this mechanochemical protocol. This direct synthesis platform has been applied to the synthesis of active pharmaceutical ingredients (APIs) and agrochemicals as well as the gram-scale synthesis of an active pharmaceutical, all in the absence of a reaction solvent.

Catalyst-free synthesis of phenanthridinesviaelectrochemical coupling of 2-isocyanobiphenyls and amines

Catalyst free synthesis of 6-aryl phenanthridines and amides through an electrochemical reaction is reported in this study. The coupling reaction proceeds by the cathodic reduction ofin situformed diazonium ions, which are formed from anilines and an alkyl nitrite. The generated aryl radical diazonium ions coupled from isocyanides furnished the desired products in good yields. This cascade reaction was conducted in an undivided cell equipped with an RVC as the anode and Pt as the cathode usingnBu4NBF4as the electrolyte at room temperature. A series of detailed mechanistic studies have also been performed, including a radical clock experiment and cyclic voltammetry analysis.

Preparation of Carbamates, Esters, Amides, and Unsymmetrical Ureas via Br?nsted Acid-Activated N-Acyl Imidazoliums

We report the application of Br?nsted acid-activated N-acyl imidazoliums as versatile intermediates in carbonyl transformations. The efficient and scalable procedure was validated on a diverse set of carbamates, esters, amides, and unsymmetrical ureas (21 examples, up to 91% yield). Additionally, we exemplify this method on multikilogram scale for the synthesis of an electron-deficient carbamate.

A case study of Pd?Pd intramolecular interaction in a benzothiazole based palladacycle; catalytic activity toward amide synthesisviaan isocyanide insertion pathway

An acetate bridge benzothiazolepalladacycle containing a rare metallophilic intramolecular Pd?Pd interaction was synthesized and thoroughly characterized. The synthesized benzothiazolepalladacycle directly anchored on SBA-15 to form an efficient heterogen

Copper and N-Heterocyclic Carbene-Catalyzed Oxidative Amidation of Aldehydes with Amines

A one-pot two-step oxidative process has been developed for the tert-butyl hydroperoxide mediated transformation of aldehydes and amines into amides catalyzed by copper(I) iodide and an N-heterocyclic carbene. The process is additive-free and does not require the amine to be transformed into its hydrochloride salts. The method is simple and practicable, has a broad substrate scope, and uses economical, feasible, and abundant reagents.

Chiral Br?nsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles

A new chiral Br?nsted acid, generated in situ from a chiral phosphoric acid boron (CPAB) complex and water, was successfully applied to asymmetric indole reduction. This “designer acid catalyst”, which is more acidic than TsOH as suggested by DFT calculations, allows the unprecedented direct asymmetric reduction of C2-aryl-substituted N-unprotected indoles and features good to excellent enantioselectivities with broad functional group tolerance. DFT calculations and mechanistic experiments indicates that this reaction undergoes C3-protonation and hydride-transfer processes. Besides, bulky C2-alkyl-substituted N-unprotected indoles are also suitable for this system.