70971-72-1

Upstream product

• 109-97-7 pyrrole 
• 100-07-2 4-methoxy-benzoyl chloride 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 201230-82-2 carbon monoxide 
• 54582-33-1 1,1'-carbonyldiimidazole 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 39108-80-0 N,N-diallyl-4-methoxybenzamide 
• 123-11-5 4-methoxy-benzaldehyde 
• 1370360-26-1 4-methoxy-N-(2,4,4-trimethoxybutyl)benzamide 
• 696-62-8 para-iodoanisole 
• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 3424-93-9 4-methoxyphenylacetamide 

Downstream Products

• 23694-49-7 1-(4-methoxybenzyl)-1H-pyrrole 
• 611-94-9 4-Methoxybenzophenone 
• 121-98-2 methyl 4-methoxybenzoate 
• 69856-75-3 1-(4-methoxyphenyl)-2-phenyl-2-(pyridin-4-yl)ethan-1-one 
• 90-96-0 bis(p-methoxyphenyl)methanone 

Relevant academic research and scientific papers

Direct C2-arylation ofN-acyl pyrroles with aryl halides under palladium catalysis

C2-arylation ofN-acyl pyrroles with aryl halides is developed for the first time using Pd(PPh3)4as a catalyst in combination with Ag2CO3under air, which allowed the application of a good compatibility catalytic system. This protocol provides a straightforward method for the preparation of valuable arylated pyrroles in moderate to good yields under the standard conditions with good substrate tolerance. Interestingly, whileN-benzoyl pyrroles reacted well, the use of substrates with a thiophene or furan ring indicated that the thiophene and furan rings are more reactive than pyrrole for the present catalytic system.

Direct oxidative coupling of: N -acyl pyrroles with alkenes by ruthenium(ii)-catalyzed regioselective C2-alkenylation

Ruthenium(ii)-catalyzed oxidative coupling by C2-alkenylation of N-acyl pyrroles with alkenes has been described. The acyl unit was found to be an effective chelating group for the activation of aryl C-H bonds ortho to the directing group. The alkenylation reaction of benzoyl pyrroles occurred regioselectively at the C2-position of the pyrrole ring, without touching the benzene ring. The reaction provides exclusively monosubstituted pyrroles under the optimized conditions. Disubstituted pyrroles could be obtained using higher loadings of the ruthenium(ii)-catalyst and the additives.

Synthesis of N -Sulfonyl- and N -Acylpyrroles via a Ring-Closing Metathesis/Dehydrogenation Tandem Reaction

N -Sulfonyl- and N -acylpyrroles were synthesized via olefin ring-closing metathesis of diallylamines and in situ oxidative aromatization in the presence of the ruthenium Grubbs catalyst and a suitable copper catalyst. In the presence of Cu(OTf) 2/s

Oxidative organocatalytic chemoselective: N -acylation of heterocycles with aromatic and conjugated aldehydes

Selective acylation of indoles is cumbersome often involving the need for sensitive and reactive acyl chloride derivatives or coupling reagents. Here we report a mild, functional group tolerant and highly chemoselective oxidative carbene catalyzed N-acylation of indoles with aldehydes. The acylation has a broad substrate scope and is compatible with substituents on both the aldehyde and the indole reaction partner. Furthermore, aza-heterocycles such as pyrrole and indazole can also be used as nucleophiles in this reaction providing the corresponding amide congeners in good yield.

Ni-Catalyzed cross-coupling reactions of N-acylpyrrole-type amides with organoboron reagents

The catalytic conversion of amides to ketones is highly desirable yet challenging in organic synthesis. We herein report the first Ni/bis-NHC-catalyzed cross-coupling of N-acylpyrrole-type amides with arylboronic esters to obtain diarylketones. This method is facilitated by a new chelating bis-NHC ligand. The reaction tolerates diverse functional groups on both arylamide and arylboronic ester partners including sensitive ester and ketone groups.

Suzuki-Miyaura Cross-Coupling of N-Acylpyrroles and Pyrazoles: Planar, Electronically Activated Amides in Catalytic N-C Cleavage

The formation of C-C bonds from amides by catalytic activation of the amide bond has been thus far possible by steric distortion. Herein, we report the first example of a general Pd-catalyzed Suzuki-Miyaura cross-coupling of planar amides enabled by the combination of (i) electronic-activation of the amide nitrogen in N-acylpyrroles and pyrazoles and (ii) the use of a versatile Pd-NHC catalysis platform. The origin and selectivity of forming acylmetals, including the role of twist, are discussed.

A practical preparation of highly versatile N-acylpyrroles from 2,4,4-trimethoxybutan-1-amine

A novel method for the preparation of N-acylpyrrole is described. The method involves condensation of carboxylic acids with 2,4,4-trimethoxybutan-1- amine, followed by acid-mediated cyclization to form the pyrrole ring. The preparative procedure is highly

Synthesis of acyl pyrroles via palladium-catalyzed carbonylative amination of aryl and alkenyl iodides

A palladium-catalyzed synthesis of acyl pyrroles from aryl and alkenyl iodides is reported. This carbonylative amination requires only atmospheric (balloon) pressure of carbon monoxide and proceeds with Pd(PPh3) 4 and Pd-NHC catalyst

Iron-catalyzed inexpensive and practical synthesis of N-substituted pyrroles in water

An operationally simple, practical, and economical protocol for iron(III) chloride catalyzed Paal-Knorr pyrrole synthesis in water in good to excellent yields has been developed. Several N-substituted pyrroles are readily prepared from the reaction of 2,5-dimethoxytetrahydrofuran and aryl/alkyl, sulfonyl and acyl amines under very mild reaction conditions. Georg Thieme Verlag Stuttgart.

Efficient carbonylation of aryl and heteroaryl bromides using a palladium/diadamantylbutylphosphine catalyst

A general palladium-catalyzed alkoxycarbonylation of aryl and heteroaryl bromides has been developed in the presence of bulky monodentate phosphines. Studies of the butoxycarbonylation of three model substrates revealed the advantages of di-1-adamantyl-n-butylphosphine compared to other ligands. In the presence of this catalyst system various bromoarenes provided the corresponding benzoic acid derivatives (ester, amides, acids) in excellent yield at low catalyst loadings (0.5 mol% Pd or below).