25563-14-8

Upstream product

• 57139-34-1 (Z)-O-methyl-p-chlorobenzohydroximoyl chloride 
• 67-62-9 O-Methylhydroxylamin 
• 122-01-0 4-chloro-benzoyl chloride 
• 593-56-6 N-methoxylamine hydrochloride 
• 74-11-3 para-chlorobenzoic acid 
• 108-67-8 1,3,5-trimethyl-benzene 
• 57139-20-5 potassium p-chlorobenzohydroxyamate 
• 74-88-4 methyl iodide 

Downstream Products

• 1202932-79-3 4-chloro-N,2-dimethoxybenzamide 
• 1202932-89-5 4-chloro-2-ethoxy-N-methoxybenzamide 
• 155694-56-7 (E)-4-chloro-2-styrylbenzamide 
• 162192-37-2 N-(3,5-dimethylbenzyl)-N-methoxy-4-chlorobenzamide 
• 1141-35-1 2-(4-chlorophenyl)benzoxazole 
• 1456693-86-9 5-chloro-3-hydroxy-2-methoxy-3-phenylisoindolin-1-one 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 1581719-96-1 4-chloro-N-methoxy-2-((triisopropylsilyl)ethynyl)benzamide 
• 1609939-43-6 6-chloro-2-methoxy-3-phenylisoquinolin-1(2H)-one 
• 33184-56-4 2-benzoyl-4-chlorobenzoic acid 
• 1417646-18-4 4-chloro-N-(dimethylcarbamoyl)-N-methoxybenzamide 
• 1354694-15-7 (E)-butyl 3-(2-carbamoyl-5-chlorophenyl)acrylate 
• 1364511-70-5 6-chloro-2-methoxy-3,4-diphenylisoquinolin-1(2H)-one 
• 186768-19-4 N-methoxy-N-propargyl-p-chlorobenzamide 

Relevant academic research and scientific papers

Harnessing hypervalent iodonium ylides as carbene precursors: C-H activation of: N -methoxybenzamides with a Rh(iii)-catalyst

Hypervalent iodonium ylides expeditiously generate carbenes which undergo domino intermolecular C-H activation followed by intramolecular condensation in the presence of N-methoxybenzamide as a starting material and a Rh(iii)-catalyst to afford dihydrophenanthridines. KIE studies and DFT calculations were performed to substantiate the mechanistic pathway. To extend the synthetic utilisation, fluorescent pyranoisocoumarins were achieved by using Rh(iii)-catalyzed peri-C-H/O-H activation/annulation reactions.

Cp?CoIII-catalyzed formal [4+2] cycloaddition of benzamides to afford quinazolinone derivatives

A Cp?CoIII-catalyzed arene C-H bond amidation/annulation of benzamides was developed to afford quinazolinone derivatives in one-pot with high yields and broad substrate scope. This method could be applied to the synthesis of quinazolinone drugs and late-stage modification of natural products.

Palladium-Catalyzed Inert C?H Bond Activation and Cyclocarbonylation of Isoquinolones with Carbon Dioxide Leading to Isoindolo[2,1-b]isoquinoline-5,7-Diones

A palladium-catalyzed inert C?H bond activation and cyclocarbonylation of isoquinolones leading to isoindolo[2,1-b]isoquinoline-5,7-diones under 1 atm of carbon dioxide has been developed. This transformation features high regio- and chemo-selectivity, step-economy, and good functional group tolerance. Most of the corresponding products were obtained in moderate to good yields. It offers an alternative approach for the synthesis of useful diverse isoindolo[2,1-b]isoquinoline-5,7-dione derivatives. (Figure presented.).

Three-Component Synthesis of Isoquinoline Derivatives by a Relay Catalysis with a Single Rhodium(III) Catalyst

A rhodium(III)-catalyzed one-pot three-component reaction of N-methoxybenzamide, α-diazoester, and alkyne was developed, providing an alternative way to synthesize isoquinoline derivatives. Mechanistically, it is a relay catalysis, and the reaction occurred via successive O-alkylation and C-H activation processes, both of which were promoted by the same catalyst.

Rhodium(III)-catalyzed chemodivergent annulations between: N-methoxybenzamides and sulfoxonium ylides via C-H activation

Chemodivergent and redox-neutral annulations between N-methoxybenzamides and sulfoxonium ylides have been realized via Rh(iii)-catalyzed C-H activation. The sulfoxonium ylide acts as a carbene precursor, and coupling occurs under acid-controlled condition

C-F bond cleavage enabled redox-neutral [4+1] annulation via C-H bond activation

Using α,α-difluoromethylene alkyne as a nontraditional one-carbon reaction partner, a synthetically novel method for the construction of isoindolin-1-one derivatives via Rh(III)-catalyzed [4+1] annulation reaction is reported. The 2-fold C-F bond cleavage not only enables the generation of desired product under an overall oxidant-free condition but also results in a net migration of carbon-carbon triple bond. In addition, the present reaction protocol exhibits a tolerance of a wide spectrum of functional groups due to the mild reaction conditions employed.

Selective mono-alkylation of N-methoxybenzamides

We report our latest discovery of norbornene derivative modulated highly mono-selective ortho-C-H activation alkylation reactions on arenes bearing simple mono-dentate coordinating groups. The reaction features the use of readily available benzamides and alkyl halides. During the study, we prepared 30 mono-alkylated aryl amides in good yields with good mono-selectivity. We have also demonstrated that structurally rigid alkenes such as norbornene and its derivatives are a good class of ligand and could be used for future direct C-H functionalizations. The utilization of norbornene type ligands for assistance in C-H activation processes has opened a new window for future molecular design using direct C-H functionalization strategies.

Palladium-Nanoparticles-Catalyzed Oxidative Annulation of Benzamides with Alkynes for the Synthesis of Isoquinolones

A novel method to synthesize isoquinolones via oxidative annulation of N-alkoxy benzamides and alkynes using binaphthyl-stabilized palladium nanoparticles (Pd-BNP) as catalyst has been developed. This methodology affords various isoquinolone derivatives in good to excellent yields with high regioselectivities in the presence of air as oxidant. N-Methoxybenzothioamide was also found to undergo oxidative annulation with alkyne successfully and provided a sulfur analogue of isoquinolones in moderate yields. The Pd-BNP catalyst was easily recovered and reused up to four times without any apparent agglomeration. (Figure presented.).

Rh-Catalyzed annulations of: N -methoxybenzamides with ketenimines: Synthesis of 3-aminoisoindolinones and 3-diarylmethyleneisoindolinones with strong aggregation induced emission properties

Rhodium-catalyzed C-H activation/annulation reactions of ketenimines with N-methoxybenzamides furnished 3-aminoisoindolin-1-ones and 3-(diarylmethylene)isoindolin-1-ones. The synthesized 3-(diarylmethylene)isoindolin-1-ones exhibited aggregation induced emissions in aqueous tetrahydrofuran solution and strong green-yellow emissions in solids.

Regiocontrolled Coupling of Aromatic and Vinylic Amides with α-Allenols to Form γ-Lactams via Rhodium(III)-Catalyzed C-H Activation

A mild, regiocontrolled coupling of aromatic and vinylic amides with α-allenols to form γ-lactams via rhodium(III)-catalyzed C-H activation has been demonstrated. This [4 + 1] annulation reaction provides an efficient method for the synthesis of isoindolinones and 1,5-dihydro-pyrrol-2-ones bearing a tetrasubstituted carbon atom α to the nitrogen atom with good functional group tolerance. The hydroxyl group in the allene substrate is essential in controlling the chemo- and regioselectivity of the reaction probably by coordination interaction with the rhodium catalyst.