136146-68-4

Upstream product

• 96-54-8 N-Methylpyrrole 
• 637-87-6 1-Chloro-4-iodobenzene 
• 106-47-8 4-chloro-aniline 
• 1204518-00-2 (4-chlorophenyl)(mesityl)iodonium trifluoromethanesulfonate 
• 95827-00-2 1-(4-chlorophenyl)but-3-en-1-one 
• 136146-93-5 p-Chlorophenyl(3-bromo-2-methoxypropyl)ketone 
• 74-89-5 methylamine 
• 110213-25-7 C₆H₄ClN₂O^(1-)*Na⁽¹⁺⁾ 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 106-39-8 bromochlorobenzene 
• 6123-05-3 C₆H₆NO₂^(1-)*K⁽¹⁺⁾ 

Downstream Products

• 1429493-48-0 2,5-bis(4-chlorophenyl)-1-methylpyrrole 
• 1080025-68-8 2-(4-chlorophenyl)-1-methyl-4-(tricyanoethenyl)-1H-pyrrole 
• 1080025-63-3 2-(4-chlorophenyl)-1-methyl-3-(tricyanoethenyl)-1H-pyrrole 
• 1080025-58-6 2-(4-chlorophenyl)-1-methyl-5-(tricyanoethenyl)-1H-pyrrole 

Relevant academic research and scientific papers

Selective synthesis of pyrrolo[1,2-a] azepines or 4,6-dicarbonyl indoles via tandem reactions of alkynones with pyrrole derivatives

Novel methodologies for the selective synthesis of pyrrolo[1,2-a]azepines or 4,6-dicarbonyl indoles starting from pyrrole derivatives and alkynones are described. When reactions were carried out with 1,2,4-trisubstituted N-propargyl pyrroles using a ZnI2 catalyst, pyrrolo[1,2-a]azepines were obtained. Whereas 4,6-dicarbonyl indoles were produced selectively with 1,2-disubstituted pyrroles in the presence of silica gel. The reaction outcomes depend on the substituent pattern of the substrates and the nature of the catalysts chosen. Control reactions suggested that the formation of a conjugated enamine intermediate was crucial for both the processes. With easily accessible starting materials, inexpensive catalysts and an easy-to-handle procedure, this reaction has the potential to become a general protocol for the synthesis of pyrrolo[1,2-a]azepines or indoles.

Tailorable carbazolyl cyanobenzene-based photocatalysts for visible light-induced reduction of aryl halides

Herein, a series of carbazolyl cyanobenzene (CCB)-based organic photocatalysts with a broad range of photoredox capabilities were designed and synthesized, allowing precise control of the photocatalytic reactivity for the controllable reduction of aryl halides via a metal-free process. The screened-out CCB (5CzBN), a metal-free, low-cost, scalable and sustainable photocatalyst with both strong oxidative and reductive ability, exhibits superior performance for both dehalogenation and C[sbnd]C bond-forming arylation reactions.

Generation of Aryl Radicals from Aryl Halides: Rongalite-Promoted Transition-Metal-Free Arylation

A new and practical method for the generation of aryl radicals from aryl halides is reported. Rongalite as a novel precursor of super electron donors was used to initiate a series of electron-catalyzed reactions under mild conditions. These transition-metal-free radical chain reactions enable the efficient formation of C-C, C-S, and C-P bonds through homolytic aromatic substitution or SRN1 reactions. Moreover, the synthesis of antipsychotic drug Quetiapine was performed on gram scale through the described method. This protocol demonstrated its potential as a promising arylation method in organic synthesis.

Radical Arylation of Anilines and Pyrroles via Aryldiazotates

The radical arylation of anilines and pyrroles can be achieved under transition-metal- and catalyst-free conditions by using aryldiazotates in strongly alkaline aqueous solutions. The aryldiazotates act as protected diazonium ions, which do not undergo azo coupling with electron-rich aromatic substrates, but can still serve as an aryl radical source at slightly elevated temperatures. Based on an improved preparation of aryldiazotates in aqueous solution, homolytic aromatic substitutions of anilines and pyrroles were conducted with good overall yields and high regioselectivity. Moreover, DFT calculations provided further mechanistic insights.

Visible-light photocatalyzed synthesis of 2-aryl N-methylpyrroles, furans and thiophenes utilizing arylsulfonyl chlorides as a coupling partner

Visible-light (Blue LED lamp: hν=425±15 nm) photocatalyzed cross-coupling reactions of arylsulfonyl chloride with N-methylpyrrole, furan, thiophene and their derivatives have been achieved in moderate to good yields at room temperature. A plausible mechan

Palladium-catalysed direct desulfitative arylation of pyrroles using benzenesulfonyl chlorides as alternative coupling partners

The reactivity of pyrrole derivatives for palladium-catalysed desulfitative arylation has been investigated. 1-Methyl-, 1-phenyl- and 1-benzylpyrroles were successfully coupled with a variety of benzenesulfonyl chlorides using a phosphine-free catalyst. Highly regioselective arylations at carbon C2 of pyrroles were observed in all cases. A wide variety of substituents on the benzenesulfonyl derivative was tolerated. It should be noted that even bromo- and iodo-benzenesulfonyl chlorides were successfully coupled with pyrrole derivatives without cleavage of the C-Br or C-I bonds, allowing further transformations. Surprisingly, with indoles, mixtures of C2- and C3-arylation products were obtained.

Room-temperature arylation of arenes and heteroarenes with diaryliodonium salts by photoredox catalysis

Aryl radicals produced by irradiation of diaryliodonium salts with visible light under the catalysis of [Ru(bpy)3]2+ undergo coupling with a wide range of arenes and heteroarenes, affording various biaryls through direct C-H arylation at room temperature. Georg Thieme Verlag Stuttgart · New York.

Visible light-mediated direct arylation of arenes and heteroarenes using diaryliodonium salts in the presence and absence of a photocatalyst

Diaryliodonium salts have been used as aryl radical sources under visible light-mediated photoredox catalysis. Benzene and a range of heteroarenes are arylated with Ar2I+ in the presence of [Ir(ppy)2(bpy)] PF6 upon irradiation with visible light. When pyrroles are used, the arylation proceeds in the absence of a photoredox catalyst. Both processes are initiated by photoinduced single-electron-transfer to Ar2I+, generating aryl radicals.

Expanded scope of heterocyclic biaryl synthesis via a palladium-catalysed thermal decarboxylative cross-coupling reaction

The palladium-catalysed decarboxylative cross-coupling of heterocyclic aromatic carboxylates and aryl halides is described. The cross-coupling proceeds under relatively mild conditions using catalytic Pd(0) and tetrabutylammonium bromide (TBAB). Utilizing

SYNTHESIS OF 1-ALKYL-2-ARYLPYRROLES FROM ARYL(3-BROMO-2-METHOXYPROPYL)KETONES

Aryl(3-bromo-2-methoxypropyl)ketones have been obtained by bromination of allylarylketones using N-bromosuccinimide.When treated with primary amines, good yields of 1-alkyl-2-arylpyrroles were obtained via 1,3-dehydrobromination and subsequent opening of