65241-92-1

Upstream product

• 838-40-4 2,5-diphenyl-1H-pyrrole 
• 106-43-4 para-chlorotoluene 
• 2089-33-0 4-methylacethophenone oxime 
• 177750-08-2 1-(4-methylphenyl)ethenylacetamide 
• 16483-98-0 2,3-diphenyl-2H-azirine 
• 122-00-9 para-methylacetophenone 
• 60295-09-2 4'-methylacetophenone carbo-t-butoxyhydrazone 
• 501-65-5 diphenyl acetylene 
• 451-40-1 phenyl benzyl ketone 
• 89108-49-6 1-(1-azidovinyl)-4-methyl benzene 
• 100-46-9 benzylamine 
• 14939-05-0 1-phenyl-3-(4-methylphenyl)prop-2-yn-1-one 
• 99275-57-7 1,2-diphenyl-4-p-tolyl-but-2-ene-1,4-dione 

Downstream Products

• 65241-96-5 2',3'-epoxy-4,5,4',5'-tetraphenyl-3,2'-di-p-tolyl-2',3'-dihydro-1H,1'H-[2,3']bipyrrolyl 
• 65241-93-2 4,4',5,5'-tetraphenyl-2,2'-di-(p-tolyl)-3,3'-dipyrryl 
• 65241-94-3 2',3-di-p-tolyl-4,4',5,5'-tetraphenyl-2,3'-dipyrryl 
• 65241-95-4 1,6a-dihydro-8-methyl-2,3,4,5-tetraphenyl-6a-(p-tolyl)benzopyrrolo<3,2-e>indole 

Relevant academic research and scientific papers

Synthesis of 2,2,5-Trisubstituted 2 H-Pyrroles and 2,3,5-Trisubstituted 1 H-Pyrroles by Ligand-Controlled Site-Selective Dearomative C2-Arylation and Direct C3-Arylation

Palladium-catalyzed site-selective dearomative C2-arylation of 2,5-diaryl-1H-pyrroles with aryl chlorides was accomplished, and a series of 2,2,5-triaryl-2H-pyrroles were synthesized. In addition, the site selectivity of the reaction was switched by simply changing the ligand, and the direct C3-arylated 2,3,5-triaryl-1H-pyrroles were prepared. The obtained 2,2,5-triaryl-2H-pyrroles could be further transformed into 2,2,5,5-tetraarylpyrrolidines.

Base-Promoted Oxidative Dearomatization of Pyrroles to 4-Pyrrolin-2-ones

A base-promoted oxidative dearomatization of substituted pyrroles for the synthesis of 3,3-disubstituted 4-pyrrolin-2-ones under mild reaction conditions is described. A cascade aerobic oxidation/semipinacol rearrangement reaction was involved, and the desired products bearing a quaternary carbon center were efficiently prepared using molecular oxygen (O2) as an ideal oxidant. (Figure presented.).

Iron-Catalyzed Radical Cycloaddition of 2H-Azirines and Enamides for the Synthesis of Pyrroles

A novel and efficient Fe-catalyzed radical cycloaddition of 2H-azirines and enamides for the synthesis of substituted pyrroles has been developed. The radical cycloaddition reaction proceeded through a conceptually new Fe(II)-catalyzed homolytic cleavage of C-N bond of 2H-azirines sequential radical cyclization with enamides. The reaction used readily available starting materials, tolerated various functional groups, and afforded valuable triaryl-substituted pyrroles in good to high yields under mild reaction conditions.

Rhodium-Catalyzed Oxidative Cycloaddition of N-tert-Butoxycarbonylhydrazones with Alkynes for the Synthesis of Functionalized Pyrroles via C(sp3)–H Bond Functionalization

A rhodium(III)-catalyzed cycloaddition of N-tert-butoxycarbonylhydrazones with internal alkynes was developed. The reaction features a regioselective α-imino alkyl C(sp3)?H bond functionalization resulting in selective formation of highly functionalized NH-free pyrroles. Our studies showed that utilizing the N-tert-butoxycarbonyl (N-Boc) as the oxidizing directing group is critical for achieving the observed pyrrole formation versus the isoquinoline formation. To account for the pyrrole formation, we hypothesized that a prior tautomerization of the N-Boc-hydrazones to enamines should occur, followed by regioselective C(sp2)–H cleavage to form a putative five-membered rhodacycle. Subsequent coupling of the rhodacycle with the alkynes would afford the pyrrole products. (Figure presented.).

Copper-catalyzed C(sp3)-H functionalization of ketones with vinyl azides: synthesis of substituted-1H-pyrroles

Copper-catalyzed C(sp3)-H functionalization of ketones with vinyl azides for the synthesis of substituted pyrroles has been developed. The method is a straightforward and efficient way to access a series of 2,3,5-trisubstituted-1H-pyrroles in modest to excellent yields with broad functional group tolerance under mild conditions.

Synthesis of multi-substituted pyrroles using enamides and alkynes catalyzed by Pd(OAc)2 with molecular oxygen as an oxidant

A cyclization reaction between enamides and alkynes catalyzed by palladium(ii) acetate is described. In this method, the molecular oxygen serves as an efficient oxidant for the Pd(ii)/Pd(0) catalytic cycle. The simple reaction conditions permit this methodology to be used as a general tool for the preparation of multi-substituted pyrroles.

One pot regiospecific synthesis of polysubstituted pyrroles from benzylamines and ynones under metal free conditions

A convenient one-pot weak base-promoted synthesis of polysubstituted pyrroles has been developed from benzylamines and ynones. This transformation involves the Michael addition reaction and intramolecular condensation, which features high regioselectivity, high efficiency, environmental friendliness and metal free. A series of polysubstituted pyrroles were provided in up to 91% yield for 27 examples.

Studies in microwave mediated solvent-free synthesis of 5-aryl-2,3-diphenylpyrroles from 4-aryl-1,2-diphenyl-2-butene-1,4-diones

4-Aryl-1.2-diphenyl-2-butene-l,4-diones and ammonium formate when irradiated with microwaves furnish 5-aryl-2.3-diphenylpyrroles in good yield under solvent-free conditions.