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Relevant academic research and scientific papers

ON THE REGIOSELECTIVITY OF THE NUCLEOPHILIC AROMATIC PHOTOSUBSTITUTION OF 4-NITROANISOLE. A DUAL MECHANISTIC PATHWAY

4-Nitroanisole photoreacts with n-hexylamine and ethyl glycinate giving rise to regioselective methoxy and nitro group photosubstitutions respectively.Mechanistic evidences indicate the last is produced through a SN23Ar* reaction whereas the first arises from a radical ion pair via electron transfer from the amine to a 4-nitroanisole triplet excited state.

Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction

The invention provides a ligand compound capable of being used for copper catalyzed aryl halide coupling reaction, the ligand compound is a three-class compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group, and the invention also provides a catalytic system for the aryl halide coupling reaction. Thecatalytic system comprises a copper catalyst, a compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group adopted as a ligand, alkali and a solvent, and meanwhile, the invention also provides a system for the aryl halide coupling reaction adopting the catalyst system. The compound containing the 2-(substituted or non-substituted) aminopyridine nitrogen oxygen group can be used as the ligand for the copper catalyzed aryl chloride coupling reaction, and the ligand is stable under a strong alkaline condition and can well maintain catalytic activity when being used for the copper-catalyzed aryl chloride coupling reaction. In addition, the copper catalyst adopting the compound as the ligand can particularly effectively promote coupling of copper catalyzed aryl chloride and various nucleophilic reagents which are difficult to generate under conventional conditions, C-N, C-O and C-S bonds are generated, and numerous useful small molecule compounds are synthesized. Therefore, the aryl halide coupling reaction has a very good large-scale application prospect by adopting the copper catalysis system of the ligand.

CuI/2-Aminopyridine 1-Oxide Catalyzed Amination of Aryl Chlorides with Aliphatic Amines

A class of 2-aminopyridine 1-oxides are discovered to be effective ligands for the Cu-catalyzed amination of less reactive (hetero)aryl chlorides. A wide range of functionalized (hetero)aryl chlorides reacted with various aliphatic amines to afford the desired products in good to excellent yields under the catalyst of CuI/2-aminopyridine 1-oxides. Furthermore, the catalyst system worked well for the coupling of cyclic secondary amines and N-methyl benzylamine with (hetero)aryl chlorides.

Regiospecific N-Arylation of Aliphatic Amines under Mild and Metal-Free Reaction Conditions

A transition metal-free N-arylation of primary and secondary amines with diaryliodonium salts is presented. Both acyclic and cyclic amines are well tolerated, providing a large set of N-alkyl anilines. The methodology is unprecedented among metal-free methods in terms of amine scope, the ability to transfer both electron-withdrawing and electron-donating aryl groups, and efficient use of resources, as excess substrate or reagents are not required.

Room-temperature Cu-catalyzed: N -arylation of aliphatic amines in neat water

A room-temperature and PTC-free copper-catalyzed N-arylation of aliphatic amines in neat water has been developed. Using a combination of CuI and 6,7-dihydroquinolin-8(5H)-one oxime as the catalyst and KOH as the base, a wide range of aliphatic amines are arylated with various aryl and heteroaryl halides to give the corresponding products in up to 95% yield.

Efficient synthetic route to aromatic secondary amines: Via Pd/RuPhos/TBAB-catalyzed cross coupling

Herein, C-N cross coupling methodology was developed for the synthesis of a diverse range of nitro-substituted secondary amines. A variety of strained, aliphatic, and aromatic precursors were effectively used, with low catalyst and ligand loading ratios resulting in product formation in good yield. This method can act as an alternative to nucleophilic addition reactions. To cross couple electron-donating, electron-withdrawing, neutral, and aliphatic primary amines with alkyl/aryl halides, a combination of RuPhos and TBAB was carefully tuned. Further, characterization of these molecules was carried out using FT-IR, 1H-NMR, 13C-NMR, 19F-NMR, single crystal XRD, and C, H, and N elemental analyses.

New ligands for copper-catalyzed C-N coupling reactions with aryl halides

2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide was identified as an efficient novel ligand for the copper-catalyzed coupling reactions of aryl iodides, bromides, and chlorides with aliphatic amines and N-containing heterocycles under mild conditions. The catalytic system showed great functional-group tolerance and excellent chemoselectivity. 7copy; 2012 Elsevier Ltd. All rights reserved.

Two Component Recyclable Heterogeneous Catalyst, Process for Preparation Thereof and its Use for Preparation of Amines

The invention describes the development of highly efficient, recyclable two component system, CuAl-hydrotalcite/rac 1,1′-Binaphthalene-2,2′-diol catalytic system for the N-alkylation of electron deficient aryl chlorides in presence of potassium carbonate as a base at room temperature in 3-6 h, wherein the process is provided for the preparation of various secondary amines via C—N coupling reaction of aliphatic amines(aliphatic open chain, acyclic, benzyl amines and heterocyclic amines) with various aryl chlorides.

Ligands for copper-catalyzed C-N bond forming reactions with 1 Mol% CuBr as catalyst

Several new ligands were designed to promote copper-catalyzed Ullman C-N coupling reactions. In this group, 8-hydroxyquinolin-N-oxide was found to serve as a superior ligand for CuBr-catalyzed coupling reactions of aryl iodides, bromides, and chlorides with aliphatic amines and N-heterocycles under a low catalyst loading (1% [Cu] mol). Reactions with the inexpensive catalytic system display a high functional group tolerance as well as excellent chemoselectivity.

Selective N-alkylation of aromatic primary amines catalyzed by bio-catalyst or deep eutectic solvent

Biocatalysts or deep eutectic solvents (DES) are effective for selective N-alkylation of various aromatic primary amines. These methods avoided complexity of multiple alkylations giving products in good yields. Both DES and lipase can be recycled and re-used at least five times. In addition, these catalysts are biodegradable, non-toxic and cost-effective.