53646-88-1

Upstream product

• 201230-82-2 carbon monoxide 
• 40032-57-3 N-(3-phenylprop-2-ynyl)benzenemethanamine 
• 139387-01-2 2-chloro-3-phenylcyclopropanecarboxaldehyde 
• 100-46-9 benzylamine 
• 61923-84-0 1,5-Dihydro-1-benzyl-4-phenyl-2H-pyrrol-2-one 
• 91153-93-4 (2E)-2-phenylbut-2-ene-1,4-diol 
• 2051-97-0 1-benzyl-1H-pyrrole 
• 108-94-1 cyclohexanone 
• 1196-67-4 (E)-β-methylcinnamaldehyde 
• 591-50-4 iodobenzene 
• 139387-02-3 (2-Chloro-3-phenyl-cyclopropyl)-methanol 
• 72733-58-5 1-hydroxymethyl-3,3-dichloro-2-phenylcyclopropane 
• 57976-72-4 2,2-dichloro-3-phenyl-cyclopropanecarboxaldehyde 
• 439813-83-9 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(benzyl)-1H-pyrrole 

Relevant academic research and scientific papers

Arylation of indoles using cyclohexanones dually-catalyzed by niobic acid and palladium-on-carbons

3-Arylindoles were easily constructed from indoles and cyclohexanone derivatives using a combination of catalytic niobic acid-on-carbon (Nb2O5/C) and palladium-on-carbon (Pd/C) under heating conditions without any oxidants. The Lewis acidic Nb2O5/C promoted the nucleophilic addition of indoles to the cyclohexanones, and the subsequent dehydration and Pd/C-catalyzed dehydrogenation produced the 3-arylindoles. The additive 2,3-dimethyl-1,3-butadiene worked as a hydrogen acceptor to facilitate the dehydrogenation step.

Pd-catalyzed imine-directed intramolecular C–N bond formation through C(sp3)–H activation: An efficient approach to multisubstituted pyrroles

An atom-economic approach to synthesize 1,2,4-trisubstituted pyrroles through palladium-catalyzed imine-directed intramolecular C(sp3)–H amination reaction has been developed. The imine group acts as a directing group as well as an intramolecular nucleophile for the first time in intramolecular C–N bonds formation reactions.

Iron-catalyzed sustainable synthesis of pyrrole

Efficient, sustainable, highly regiospecific substituted pyrroles were synthesized using a well-defined, air stable, molecular iron(0) complex. The developed methodology is broadly applicable and tolerates a variety of functional groups. C-2, C-3, and C-2 & C-4 substituted pyrroles were synthesized in good yield. Symmetrical bis-pyrroles were accessible for the first time using an iron catalyst. On the basis of the experimental observation, we propose that the reaction proceeds through a hydrogen autotransfer process followed by second oxidation/ intramolecular dehydrative condensation to provide the pyrrole.

β-selective C-H arylation of pyrroles leading to concise syntheses of lamellarins C and I

The first general β-selective C-H arylation of pyrroles has been developed by using a rhodium catalyst. This C-H arylation reaction, which is retrosynthetically straightforward but results in unusual regioselectivity, could result in de novo syntheses of

New ring expansion of cyclobutanones: Synthesis of pyrrolinones, pyrrolidines and pyrroles

2,2-Dichlorocyclobutanones reacted with various amines to give ring opening leading to 4,4-dichlorobutanamides. These compounds proved to be suitable substrates for the synthesis of 3-pyrrolin-2-ones, 2-pyrrolidinones, pyrrolidines and pyrroles.

Suzuki coupling reactions in heterocyclic chemistry: Synthesis of 3-substituted pyrrolines and pyrroles

A simple preparation of N-substituted 3-pyrroline boromic esters from primary amines is described. The Suzuki-Miyaura coupling of these heterocycles with aryl halides proceeds in good yields. Alternatively, oxidation with DDQ or MnO2, gives the

Rhodium-Catalysed Reactions of Propargylamines with CO/H2. Formation of Pyrroles and Butenolides

Rhodium-catalysed reactions of (arylpropargyl)amines with CO/H2 give β-arylpyrroles in good yields.Reactions of (alkylpropargyl)amines gave alkylpyrroles together with butenolides which are formed in an unusual reaction that probably involves double carbonylation, reduction of one carbonyl function and removal of the amine function by hydrogenolysis.The single-crystal X-ray structure of 5-methyl-N,3-diphenylpyrrole-2-carboxamide is recorded.

FORMATION OF 1-SUBSTITUTED PYRROLES IN REACTION OF 2-CHLOROCYCLOPROPANECARBOXALDEHYDES WITH PRIMARY AMINES

Reactions of 2-chlorocyclopropanecarboxaldehydes with primary amines in boiling DMF lead in good yield to 1-substituted pyrroles. 2-Chlorocyclopropanecarboxaldehydes were synthesized by the stereoselective reduction of the corresponding 2,2-dichlorocyclopropanemethanols with lithium tetrahydroaluminate with the subsequent oxidation of the mixture of stereoisomeric 2-chlorocyclopropanemethanols with pyridinium chlorochromate.