6642-37-1

Usage

InChI:InChI=1/C11H15NO2/c1-8(2)11(13)12-9-4-6-10(14-3)7-5-9/h4-8H,1-3H3,(H,12,13)

Upstream product

• 80542-40-1 N-cinnamylidene-p-anisidine 
• 81357-56-4 Thioisobutyric acid S-pyridin-2-yl ester 
• 108908-63-0 N-4-methoxyphenyl-α-methylcinnamylideneamine 
• 129397-33-7 N-(4-Methoxyphenyl)cyclohexylacetaldimine 
• 100-17-4 para-methoxynitrobenzene 
• 79-31-2 isobutyric Acid 
• 563-83-7 ISOPROPYLAMIDE 
• 623-12-1 4-chloromethoxybenzene 
• 20279-29-2 phenyl isobutyrate 
• 104-94-9 4-methoxy-aniline 
• 78-82-0 Isobutyronitrile 
• 141339-54-0 bis(4-anisyl)iodonium triflate 
• 121-97-1 4-Methoxypropiophenone 
• 2040-20-2 4-methoxyisobutyrophenone 

Downstream Products

• 14016-32-1 Dimethylketen-p-anisylimin 

Relevant academic research and scientific papers

Enantioselective One-Pot Synthesis of β-Lactams from Achiral 2-Pyridylthioesters and Aromatic Imines

The enolates derived from 2-pyridylthioesters by reaction with BCl3*SMe2 and enantiomerically pure aminoalcohols react with aromatic imines in an enantioselective fashion (ee up to 78percent) to afford β-lactams in a convenient one-pot procedure.

Ligand-free copper-catalyzed direct amidation of diaryliodonium salts using nitriles as amidation reagents

An efficient and practical methodology for the synthesis of N-arylamides has been developed via copper-catalyzed amidation of diaryliodonium salts with nitriles. Various substituted aryl nitriles and aliphatic nitriles could be applied in the reaction, providing a series of N-arylated amides in moderate to good yields. This procedure provides an alternative route for the synthesis of various N-arylamides. A proposed mechanism based on control experiments is also presented.

Preparation method of N-aryl amide compound

The invention discloses a preparation method of an N-aryl amide compound, which comprises the following steps: (1) putting diaryliodonium salt and Cu(OAc)2 into a Schlenk tube provided with a magneticstirring rod; (2) sequentially adding DCE, H2O and nitrile by using an injector, sealing the Schlenk tube, and stirring for reaction at 80 DEG C; (3) cooling the obtained solution to room temperature, and performing extraction with EtOAc; and combining organic layers, performing washing with saline water, and performing drying with anhydrous Na2SO4; and (4) removing volatile matters in vacuum, and purifying residues through column chromatography to obtain the N-aryl amide compound. Through a large number of experiments, a substrate with a simple structure is screened, the reaction conditionsare mild, the yield is high, the pollution is small, and the application prospect is wide.

Catalyst-Free Transamidation of Aromatic Amines with Formamide Derivatives and Tertiary Amides with Aliphatic Amines

A simple catalyst- and promoter-free protocol has been developed for the transamidation of weakly nucleophilic aromatic amines with formamide derivatives and low-reactivity tertiary amides with aliphatic amines. This strategy is advantageous because no catalyst or promoters are needed, no additives are required, separation and purification is easy, and the reaction is scalable. Significantly, this strategy was further applied to synthesize several pharmaceutical molecules on a gram scale, and excellent yields were achieved.

Rapidly Activating Pd-Precatalyst for Suzuki-Miyaura and Buchwald-Hartwig Couplings of Aryl Esters

Esters are valuable electrophiles for cross-coupling due to their ubiquity and ease of synthesis. However, harsh conditions are traditionally required for the effective cross-coupling of ester substrates. Utilizing a recently discovered precatalyst, Pd-catalyzed Suzuki-Miyaura and Buchwald-Hartwig reactions involving cleavage of the C(acyl)-O bond of aryl esters that proceed under mild conditions are reported. The Pd(II) precatalyst is highly active because it is reduced to the Pd(0) active species more rapidly than previous precatalysts.

Cross-Coupling of Primary Amides to Aryl and Heteroaryl Partners Using (DiMeIHeptCl)Pd Promoted by Trialkylboranes or B(C6F5)3

Boron-derived Lewis acids have been shown to effectively promote the coupling of amide nucleophiles to a wide variety of oxidative addition partners using Pd-NHC catalysts. Through a combination of NMR spectroscopy and control studies with and without oxygen and radical scavengers, we propose that boron-imidates form under the basic reaction conditions that aid coordination of nitrogen to Pd(II), which is rate limiting, and directly delivers the intermediate for reductive elimination.

Utilization of MeOH as a C1 Building Block in Tandem Three-Component Coupling Reaction

Ru(II) catalyzed tandem synthesis of α-branched methylated ketones via multicomponent reactions following the hydrogen borrowing process is described. This nonphosphine-based air and moisture stable catalyst efficiently produced various methylated ketones using methanol as a methylating agent. This system was found to be highly effective in three-component coupling between methanol, primary alcohols, and methyl ketones. A proposed catalytic cycle for the α-methylation is supported by DFT calculations as well as kinetic experiments.

Direct hydrogenation of nitroaromatics and one-pot amidation with carboxylic acids over platinum nanowires

A novel ultrathin platinum nanowire with uniform length and a diameter of 1.5 nm was synthesized by acidic etching of FePt nanowire in methanol. This nanowire was characterized by high-resolution transmission electron microscopy (HRTEM). X-ray diffraction (XRD) data indicated that the main plane is (111). The ability of this nanowire to catalyze the heterogeneous hydrogenation of nitroaromatics to give the corresponding amines has been investigated. The catalyst showed satisfactory activity in various solvents under mild conditions and showed excellent stability. The catalytic performance was also evaluated in the one-pot reduction of nitroaromatics and amidation with carboxylic acids under a hydrogen atmosphere at 100°C. These methods for the hydrogenation of nitroaromatics and the direct amidation of nitroaromatics with carboxylic acids are simple, economical, and environmentally benign, and have practical advantages for the synthesis of amines and amides without the production of toxic byproducts.