905971-72-4

Upstream product

• 1309689-00-6 C₂₄H₁₄F₅NO₂ 
• 1357170-61-6 (5-azidopent-2-yne-1,5-diyl)dibenzene 
• 98-85-1 1-Phenylethanol 
• 1795-98-8 rac-phenylalaninol 
• 3182-95-4 L-Phenylalaninol 
• 98-86-2 acetophenone 
• 38597-58-9 2-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester 
• 100-51-6 benzyl alcohol 
• 56900-73-3 phenyl(5-phenyl-1H-pyrrol-2-yl)methanone 
• 19433-17-1 acetophenone O-acetyloxime 
• 98-80-6 phenylboronic acid 
• 35281-70-0 1,5-diphenylpent-3-yn-1-ol 

Downstream Products

• 141824-66-0 (+)-(S)-5-benzyl-2-phenyl-1-pyrroline 
• 141824-66-0 (-)-(R)-5-benzyl-2-phenyl-1-pyrroline 

Relevant academic research and scientific papers

Cu-Catalyzed Cascade Cyclization of Ketoxime Acetates and Alkynals Enabling Synthesis of Acylpyrroles

A facile copper-based catalytic system has been developed to enable efficient cyclization of methylketoximes and alkynals. This protocol provides a viable entry to synthetically and pharmaceutically useful 2-acylpyrroles with a broad range of compatible functionalities. Mechanistically, a key acyl migration is probably involved that leads to the formation of N-acyl pyrroles or otherwise NH pyrroles by further hydrolysis. More importantly, the present reaction system also gives an opportunity to realize three-component pyrrole assembly by simple addition of carboxylic acid.

A robust NNP-type ruthenium (II) complex for alcohols dehydrogenation to esters and pyrroles

A Ru (II) complex bearing pyridyl-based benzimidazole-phosphine tridentate NNP ligand was synthesized and structurally characterized by NMR, IR. The complex can efficiently and selectively catalyze the acceptorless dehydrogenation of primary alcohols to esters under relatively mild conditions and the synthesis of pyrroles by means of the reactions of secondary alcohols and β-amino alcohols through acceptorless deoxygenation condensation.

Nickel-Catalyzed Double Dehydrogenative Coupling of Secondary Alcohols and β-Amino Alcohols to Access Substituted Pyrroles

Herein, we demonstrate the first nickel-catalyzed double dehydrogenative condensation of secondary alcohols and β-amino alcohols in one pot to the pyrrole derivatives. A series of 2,5- and 2,3,5-substituted pyrroles were obtained in ≤83% yield, releasing

General Transition Metal-Free Synthesis of NH-Pyrroles from Secondary Alcohols and 2-Aminoalcohols

A novel, transition metal-free and one-pot methodology to synthesize various substituted NH-pyrroles from readily available building blocks such as secondary alcohols and 2-aminoalcohols is described. The process is based on the venerable Oppenauer-Woodward oxidation, which uses benzophenone as an inexpensive reagent to achieve oxidation of secondary alcohols under mild condition to ketones, further in situ condensation with aminoalcohol, and oxidative cyclization to the target pyrrole ring. The reaction occurs under basic conditions, and features a broad substrate scope combined with very good tolerance for sensitive functional groups. This method can be used to synthesize various substituted pyrroles useful as a starting material for broad applications.

A nitrogen-ligated nickel-catalyst enables selective intermolecular cyclisation of β- And γ-amino alcohols with ketones: Access to five and six-membered N-heterocycles

Owing to the great demand for the synthesis of N-heterocycles, development of new reactions that utilise renewable resources and convert them into key chemicals using non-precious base metal-catalysts is highly desirable. Herein, we demonstrated a sustainable Ni-catalysed dehydrogenative approach for the synthesis of pyrroles, pyridines, and quinolines by the reaction of β- and γ-amino alcohols with ketones via C-N and C-C bond formations in a tandem fashion. A variety of aryl, hetero-aryl, and alkyl ketones having free amine, halide, alkyl, alkoxy, alkene, activated benzyl, and pyridine moieties were converted into synthetically interesting 2,3 and 2,3,5-substituted bicyclic as well as tricyclic N-heterocycles with up to 90% yields. As a highlight, we demonstrated the synthesis of an interesting pyrrole derivative by intermolecular cyclisation of a steroid hormone with phenylalaninol.

Catalytic C-Alkylation of Pyrroles with Primary Alcohols: Hans Fischer's Alkali and a New Method with Iridium P,N,P-Pincer Complexes

Hydrogen-autotransfer alkylation (HAT or “borrowing-hydrogen” alkylation) of heteroaromatic compounds has been studied with a range of substrates recently, but pyrroles have been largely absent from such studies. The conditions for HAT alkylations of pyrroles were investigated under a variety of conditions and were found to take place under basic alcoholic conditions (Hans Fischer alkylation) in the absence of transition-metal catalysts; by means of a heterogeneous Pd/C catalyst in the presence of base; and finally by means of homogeneous transition-metal catalysis combining a base and iridium pincer complexes generated in situ that have not previously been used in HAT alkylations of heterocycles.

A Versatile Ru(II)-NNP Complex Catalyst for the Synthesis of Multisubstituted Pyrroles and Pyridines

A pincer-type Ru(II)-NNP complex bearing a pyrazolyl-(NH-PtBu2)-pyridine ligand was synthesized and structurally characterized by NMR, IR, elemental analysis, and X-ray single-crystal crystallographic determinations, which efficiently catalyzed the synthesis of multisubstituted pyrroles and pyridines by means of the reactions of secondary alcohols and β- or γ-amino alcohols through deoxygenation and selective C-N and C-C bond formation. The coupling reactions took place with 0.3 mol % catalyst loading and tolerated diverse functional groups. The present work provides an alternative method to construct highly active transition-metal complex catalysts from readily available ligands.

Manganese-Catalyzed Sustainable Synthesis of Pyrroles from Alcohols and Amino Alcohols

The development of reactions that convert alcohols into important chemical compounds saves our fossil carbon resources as alcohols can be obtained from indigestible biomass such as lignocellulose. The conservation of our rare noble metals is of similar importance, and their replacement by abundantly available transition metals, such as Mn, Fe, or Co (base or nonprecious metals), in key technologies such as catalysis is a promising option. Herein, we report on the first base-metal-catalyzed synthesis of pyrroles from alcohols and amino alcohols. The most efficient catalysts are Mn complexes stabilized by PN5P ligands whereas related Fe and Co complexes are inactive. The reaction proceeds under mild conditions at catalyst loadings as low as 0.5 mol %, and has a broad scope and attractive functional-group tolerance. These findings may inspire others to use Mn catalysts to replace Ir or Ru complexes in challenging dehydrogenation reactions.

Cobalt-catalyzed acceptorless dehydrogenative coupling of aminoalcohols with alcohols: Direct access to pyrrole, pyridine and pyrazine derivatives

Here, the first example is reported of a new, molecularly defined SNS-cobalt(ii) catalyst for the acceptorless dehydrogenative coupling (ADC) of unprotected amino alcohols with secondary alcohols leading to pyrrole and pyridine derivatives.

Nickel-Catalyzed 1,2-Aminoarylation of Oxime Ester-Tethered Alkenes with Boronic Acids

A nickel-catalyzed 1,2-aminoarylation of oxime-ester-tethered alkenes with boronic acids was developed. A variety of pyrroline derivatives were synthesized in good yields via the successive formation of C(sp3)-N and C(sp3)-C(sp2) bonds. For cyclobutanone-derived oxime esters, the reaction provided aliphatic nitriles incorporating an aromatic group in the γ-position. A mechanism involving iminyl radical and carbon-centered radical intermediates was proposed.