93007-80-8

Upstream product

• 61650-22-4 N-(pivaloyloxy)benzamide 
• 19099-54-8 2-isopropyliodobenzene 
• 106012-41-3 N-[2-(1-methylethenyl)phenyl]benzamide 
• 52562-19-3 2-isopropenylaniline 
• 65-85-0 benzoic acid 
• 1885-29-6 anthranilic acid nitrile 
• 551-93-9 2-aminoacetophenone 
• 643-28-7 2-isopropylaniline 
• 99802-96-7 2-benzoyl-1,3-dimethyl-1H-imidazol-3-ium iodide 
• 98-88-4 benzoyl chloride 
• 30148-17-5 (1-methyl-1H-imidazol-2-yl)(phenyl)methanone 
• 2077-13-6 2-chlorocumene 
• 55-21-0 benzamide 
• 106012-47-9 4-Methyl-4-methylsulfanylmethyl-2-phenyl-4H-benzo[d][1,3]oxazine 

Downstream Products

• 106012-48-0 4,4-dimethyl-2-phenyl-4H-benzo[d][1,3]oxazine 

Relevant academic research and scientific papers

Mechanochemical Synthesis of N-Aryl Amides from O-Protected Hydroxamic Acids

Two robust and efficient mechanochemical protocols for the synthesis of an array of N-arylamides have been developed. This was achieved by a C?N cross-coupling between O-pivaloyl hydroxamic acids and aryl iodides or aryl boronic acids, in the presence of a stoichiometric amount of a copper mediator. The effectiveness of this method is highlighted by the high-yielding (up to 94 %), scalable (up to 8 mmol), and rapid (20 minutes) synthesis of N-aryl amides (15 examples), using a variety of deactivated and sterically encumbered substrates, whilst employing mild conditions and in the absence of solvents. In addition, it was determined that whilst the O-pivaloyl hydroxamic acid precursors can be synthesised mechanochemically, iron contamination originating from the steel jars was found to occur which can hinder the efficacy of this process. Furthermore, 3D printing was used to produce custom milling jars that could successfully accommodate a scaled-up version of the two protocols.

Experimental and Computational Studies on Cp*CyRh(III)/KOPiv-Catalyzed Intramolecular Dehydrogenative Cross-Couplings for Building Eight-Membered Sultam/Lactam Frameworks

Described herein is an unusual Cp*CyRh(III)-catalyzed intramolecular site-specific aryl C-H annulation, a highly chemoselective protocol providing direct access to eight-membered sultams/lactams with broad substrate/functional group tolerance. Experimental and computational studies reveal that such a transformation involves a unique PivOH-assisted aryl C-H activation/alkene insertion/β-H elimination/hydrogen-transfer process involving the Rh(III)-hydride species as the active intermediate with the concomitant release of H2 as the major byproduct, thus enabling the developed Cp*CyRh(III) catalysis with redox-neutral and highly atom-economical features.

Enantioselective Synthesis of Atropisomeric Anilides via Pd(II)-Catalyzed Asymmetric C-H Olefination

Atropisomeric anilides have received tremendous attention as a novel class of chiral compounds possessing restricted rotation around an N-aryl chiral axis. However, in sharp contrast to the well-studied synthesis of biaryl atropisomers, the catalytic asym

Clickable coupling of carboxylic acids and amines at room temperature mediated by SO2F2: A significant breakthrough for the construction of amides and peptide linkages

The construction of amide bonds and peptide linkages is one of the most fundamental transformations in all life processes and organic synthesis. The synthesis of structurally ubiquitous amide motifs is essential in the assembly of numerous important molecules such as peptides, proteins, alkaloids, pharmaceutical agents, polymers, ligands and agrochemicals. A method of SO2F2-mediated direct clickable coupling of carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in greater than 99% purity and excellent yields.

Base-Promoted Amidation and Esterification of Imidazolium Salts via Acyl C-C bond Cleavage: Access to Aromatic Amides and Esters

Imidazolium salts have been effectively employed as suitable acyl transfer agents in amidation and esterification in organic synthesis. The weak acyl C(O)-C imidazolium bond was exploited to generate acyl electrophiles, which further react with amines and alcohols to afford amides and esters. The broad substrate scope of anilines and benzylic amines and base-promoted conditions are the benefits of this route. Interestingly, phenol, benzylic alcohols, and a biologically active alcohol can also be subjected to esterification under the optimized conditions.

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.

Copper-catalyzed selective benzylic C-O cyclization of N-o-tolylbenzamides: Synthesis of 4 H-3,1-benzoxazines

A novel Selectfluor-mediated copper-catalyzed highly selective benzylic C-O cyclization for the synthesis 4H-3,1-benzoxazines is reported. The predominant selectivity for a benzylic C(sp3)-H over an aromatic C(sp 2)-H bond in N-o-tolylbenzamides is achieved.

Intramolecular Cyclisation Using Methyl(bismethylthio)sulphonium Salts. Part 3. Synthesis of 3,1-Benzoxazines.

The reaction of methyl(bismethylthio)sulphonium hexachloroantimonate (1) with 2-benzamido-, 2-acetamido-, and 2-phenylacetamido-1-isopropenylbenzene (2) - (4) leads to methylthio-functionalized 3,1-benzoxazine derivatives (8) - (10).The structures of the