82238-92-4

Usage

Uses

Used in Pharmaceutical Industry:
1-(1-Naphthyl)pyrrolidine is used as a building block in drug synthesis for its potential to create various biologically active compounds. Its unique structure allows for the development of new pharmaceutical agents with specific therapeutic properties.
Used in Organic Chemistry Research:
In the realm of organic chemistry, 1-(1-Naphthyl)pyrrolidine serves as a valuable research tool. It is utilized in the study of chemical reactions and mechanisms, contributing to a deeper understanding of organic processes.
Used as a Chiral Ligand in Asymmetric Catalysis:
1-(1-Naphthyl)pyrrolidine is employed as a chiral ligand in asymmetric catalysis. Its unique structure allows it to induce selectivity in catalytic reactions, leading to the production of enantiomerically pure compounds, which is crucial in the synthesis of pharmaceuticals and agrochemicals.
Used in Metal Complex Formation:
1-(1-Naphthyl)pyrrolidine has also been studied for its ability to form stable complexes with transition metals. The formation of these complexes can have applications in various areas, including catalysis and the development of new materials with specific properties.
Overall, 1-(1-Naphthyl)pyrrolidine plays a significant role in the advancement of drug development and organic synthesis processes, making it a valuable asset in the fields of chemistry and medicine.

InChI:InChI=1/C14H15N/c1-2-8-13-12(6-1)7-5-9-14(13)15-10-3-4-11-15/h1-2,5-9H,3-4,10-11H2

Upstream product

• 109-99-9 tetrahydrofuran 
• 134-32-7 1-amino-naphthalene 
• 110-52-1 1,4-dibromo-butane 
• 7007-34-3 1-(3,4-dihydro-1-naphthalenyl)pyrrolidine 
• 123-75-1 pyrrolidine 
• 68211-49-4 1-naphthyl tosylate 
• 321-38-0 1-Fluoronaphthalene 
• 195871-32-0 2-(2-acetylphenyl)acetaldehyde 
• 83-33-0 inden-1-one 
• 767-60-2 3-Methylindene 
• 64666-42-8 1-methyl-1-indanol 
• 86-57-7 1-Nitronaphthalene 
• 118-44-5 1-N-ethylnaphthylamine 
• 90-14-2 1-Iodonaphthalene 

Relevant academic research and scientific papers

Organic photoredox catalytic α-C(sp3)-H phosphorylation of saturated: Aza -heterocycles

A metal-free C(sp3)-H phosphorylation of saturated aza-heterocycles via the merger of organic photoredox and Br?nsted acid catalyses was established under mild conditions. This protocol provided straightforward and economic access to a variety of valuable α-phosphoryl cyclic amines by using commercially available diarylphosphine oxide reagents. In addition, the D-A fluorescent molecule DCQ was used for the first time as a photocatalyst and exhibited an excellent photoredox catalytic efficiency in this transformation. A series of mechanistic experiments and DFT calculations demonstrated that this transformation underwent a sequential visible light photoredox catalytic oxidation/nucleophilic addition process.

I2/NaH2PO2-mediated deoxyamination of cyclic ethers for the synthesis of: N -aryl-substituted azacycles

We have developed a protocol for efficient synthesis of N-aryl-substituted azacycles from aryl amines and cyclic ethers using I2/NaH2PO2 as the mediator. A diverse range of aryl amines and cyclic ethers undergo amination reaction to generate products in good to excellent yields with good functional group tolerance. This reaction can be easily scaled up to give N-aryl-substituted azacycles on a gram scale. Further chemical manipulation of the products enabled useful transformations of the quinoline ring, including bromination and acetylation. This journal is

Practical direct synthesis of: N -aryl-substituted azacycles from N -alkyl protected arylamines using TiCl4and DBU

A novel transformation of N-alkyl protected arylamines and cyclic ethers into N-aryl substituted azacycles is described. Alkyl groups have been used for the protection of amines in organic syntheses. In this synthesis, N-alkyl protected arylamines were reacted with cyclic ethers in the presence of TiCl4 and DBU, crucial reagents affording five- and six-membered azacycles. In particular, utilization of the novel TiCl4/DBU-mediated reaction allows various N-alkyl protected arylamines such as N-methyl-, N-ethyl-, N-isopropyl, and N-tert-butyl arylamines to be readily converted into N-aryl substituted azacycles in high yields. This practical approach using various N-alkyl arylamines leads to the efficient preparation of azacycles.

Visible-Light-Mediated C(sp3)–H Thiocarbonylation for Thiolactam Preparation with Potassium Sulfide

We report herein a protocol for thiolactam preparation with potassium sulfide via visible-light-mediated C(sp3)–H thiocarbonylation, in which polysulfide dianions and radical anions generated from potassium sulfide were the key active species. A variety of thiolactams were straightforward established under mild conditions. Moreover, it was successfully applied to structural modification of tetrahydroberberine.

Metal-Free Synthesis of N-Aryl-Substituted Azacycles from Cyclic Ethers Using POCl3

A facile method for the synthesis of N-aryl-substituted azacycles from arylamines and cyclic ethers has been developed. In this study, arylamines were treated with cyclic ethers in the presence of POCl3 and DBU to provide five- A nd six-membered azacycles. Using this method, various azacycloalkanes, isoindolines, and tetrahydroisoquinolines were prepared in high yields. This synthetic method offers an efficient approach to the production of azacycles from cyclic ethers.

Well-Designed N-Heterocyclic Carbene Ligands for Palladium-Catalyzed Denitrative C-N Coupling of Nitroarenes with Amines

The C-N bond formation is one of the fundamental reactions in organic chemistry, because of the widespread presence of amine moieties in pharmaceuticals and biologically active compounds. Palladium-catalyzed C-N coupling of haloarenes represents one of the most efficient approaches to aromatic amines. Nitroarenes are ideal alternative electrophilic coupling partners, since they are inexpensive and readily available. The denitration and cross-coupling using nitroarenes as the electrophilic partners is challenging, because of the low reactivity of the Ar-NO2 bond toward oxidative addition. We report here the C-N coupling of nitroarenes and amines using palladium/5-(2,4,6-triisopropylphenyl)imidazolylidene[1,5-a]pyridines as the catalyst. The ligands are readily available from commercial chemicals. The reaction shows broad substrate scope and functional group tolerance. The method is applicable to both aromatic and aliphatic amines, and many secondary and tertiary aromatic amines bearing various functional groups were obtained in high yields.

Dual C(sp3)?H Bond Functionalization of N-Heterocycles through Sequential Visible-Light Photocatalyzed Dehydrogenation/[2+2] Cycloaddition Reactions

Herein we describe a mild method for the dual C(sp3)?H bond functionalization of saturated nitrogen-containing heterocycles through a sequential visible-light photocatalyzed dehydrogenation/[2+2] cycloaddition procedure. As a complementary approach to the well-established use of iminium ion and α-amino radical intermediates, the elusive cyclic enamine intermediates were effectively generated by photoredox catalysis under mild conditions and efficiently captured by acetylene esters to form a wide array of bicyclic amino acid derivatives, thus enabling the simultaneous functionalization of two vicinal C(sp3)?H bonds.

Ultrafine hybrid Cu2O-Fe2O3 nanoparticles stabilized by hexaphenylbenzene-based supramolecular assemblies: A photocatalytic system for the Ullmann-Goldberg coupling reaction

Ultrafine hybrid Cu2O-Fe2O3 NPs have been prepared using the supramolecular assemblies of hexaphenylbenzene (HPB) derivative 3 as nanoreactors and stabilizers. The as-prepared hybrid Cu2O-Fe2O3 NPs serve as an efficient and recyclable photocatalytic system for carrying out C-N coupling between aryl halides and various amines (aliphatic, aromatic and N-heterocyclic) at room temperature in mixed aqueous media under visible light irradiation. Amazingly, Cu2O-Fe2O3 NPs also exhibited high efficiency in the reactions involving the synthesis of biologically important N-substituted carbazole derivatives. The work being presented in this article demonstrates the preparation of a 'dip strip' coated with the as-prepared catalytic system and utilization of this paper strip as a recyclable and portable heterocatalytic system for carrying out the Ullmann-Goldberg coupling.

Cycloaddition of Enamine and Iminium Ion Intermediates Formed in the Reaction of N -Arylpyrrolidines with T-HYDRO

The reaction of N-arylpyrrolidine derivatives with 70% aqueous tert-butyl hydroperoxide (T-HYDRO) in the presence of NaOAc·3H2O gives tetracyclic amines in 59-78% yields via cycloaddition of the corresponding iminium ion and enamine intermediates formed in situ in cyclohexane solvent. The iminium ion intermediate reacts with t-BuOK in methanol to give the corresponding cyclic amides in 85-88% yields or undergoes alkylation to give the corresponding nitromethyl product in 74-79% yields using t-BuOK and nitromethane in methanol.

Synthesis of N-aryl substituted, five- and six-membered azacycles using aluminum-amide complexes

Synthesis of N-aryl substituted, five- and six-membered azacycloalkanes, isoindolines and tetrahydroisoquinolines, has been described. In this synthesis, cyclic ethers (n = 1, 2) were treated with dimethylaluminum-amide reagents, derived from a range of aryl amines and trimethylaluminum, to afford the corresponding azacycles in good yields. This journal is the Partner Organisations 2014.