172940-57-7

Upstream product

• 100-61-8 N-methylaniline 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 172940-58-8 (2-([methyl(phenyl)amino]methyl)phenyl)boronic acid 
• 30319-92-7 5-methyl-5,6-dihydro-phenanthridine 
• 614-30-2 N-methyl-N-phenyl-benzenemethanamine 
• 157330-05-7 Na⁽¹⁺⁾*(OH)2B(C₆H₄)CH₂N(CH₃)C₆H₄N₂(C₆H₄)SO₃^(1-) = Na((OH)2B(C₆H₄)CH₂N(CH₃)C₆H₄N₂(C₆H₄)SO₃) 

Relevant academic research and scientific papers

Microwave assisted synthesis of phenanthridinones and dihydrophenanthridines by vasicine/KO: T Bu promoted intramolecular C-H arylation

A simple, efficient, rapid and transition metal-free methodology has been developed by utilizing vasicine (a natural product), as a catalyst for the synthesis of phenanthridinones and dihydrophenanthridines. The reaction proceeds through intramolecular C-H arylation with aryl halides in the presence of KOtBu as a base under microwave irradiation in sulfolane as a solvent. The reaction proceeds well with various aryl iodides, bromides and more remarkably with less reactive aryl chlorides for 15 minutes, providing the corresponding products in 45-90% yields.

BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant

A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug molecules and biologically relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF3and hydride transfer from formic acid.

Regioselective, Photocatalytic α-Functionalization of Amines

Photocatalytic α-functionalization of amines provides a mild and atom-economical means to synthesize α-branched amines. Prior examples featured symmetrical or electronically biased substrates. Here we report a controllable α-functionalization of amines in which regioselectivity can be tuned with minor changes to the reaction conditions.

2-Aminoquinazolin-4(3H)-one as an Organocatalyst for the Synthesis of Tertiary Amines

The potential of 2-aminoquinazolin-4(3H)-one as an organocatalyst for the activation of aldehydes via noncovalent interaction for the synthesis of tertiary amines using formic acid as a reducing agent is reported for the first time. The developed protocol demonstrated a dilated substrate scope for aromatic and aliphatic amines with aromatic and aliphatic aldehydes. Furthermore, the current method was also fruitful for the derivatization of ciprofloxacin and its derivative in good to excellent yields.

General Reductive Amination of Aldehydes and Ketones with Amines and Nitroaromatics under H2 by Recyclable Iridium Catalysts

Heterogeneous iridium catalysts were prepared and applied for the reductive amination of aldehydes and ketones with nitroaromatics and amines using H2. The iridium catalysts were prepared by pyrolysis of ionic liquid 1-methyl-3-cyanomethylimidazoulium chloride ([MCNI]Cl) with iridium chloride (IrCl3) in activated carbons. Iridium particles were well dispersed and stable in the N-doped carbon materials from [MCNI]Cl with activated carbon. The Ir@NC(600-2h) catalyst was found to be highly active and selective for the reductive amination of aldehydes and ketones using H2 and a variety of nitrobenzenes and amines were selectively converted into the corresponding secondary and tertiary amines. The Ir@NC(600-2h) catalyst can be reusable several times without evident deactivation.

Heterogeneous cobalt catalysts for reductive amination with H2: General synthesis of secondary and tertiary amines

Heterogeneous Co@NC catalysts were prepared, characterized and applied for the reductive amination of aldehydes and ketones with H2 gas. The Co catalyst Co@NC (800-2 h) was found to be active and selective for the reductive amination of aldehydes and ketones using H2 gas. Thus, general synthesis of secondary and tertiary amines was developed by the Co-catalyzed reductive amination with H2 gas, and various secondary and tertiary amines can be obtained in high yields. Moreover, a practical synthesis of N-substituted isoindolinones was also presented by a one step process with the Co@NC (800-2 h) catalyst. The Co@NC (800-2 h) catalyst is reusable at least five times without evident loss of activity.

Chemoselective reductive amination of carbonyl compounds for the synthesis of tertiary amines using SnCl2·2H2O/PMHS/MeOH

Stannous chloride catalyzed chemoselective reductive amination of a variety of carbonyl compounds with aromatic amines has been developed for the synthesis of a diverse range of tertiary amines using inexpensive polymethylhydrosiloxane as reducing agent in methanol. The present method is also applicable for the synthesis of secondary amines including heterocyclic ones.

Intramolecular direct dehydrohalide coupling promoted by KOtBu: Total synthesis of amaryllidaceae alkaloids anhydrolycorinone and oxoassoanine

A transition-metal-free intramolecular dehydrohalide coupling via intramolecular homolytic aromatic substitution (HAS) with aryl radicals has been developed in the presence of potassium tert-butoxide and an organic molecule as the catalyst. The methodology has been applied to a concise synthesis of Amaryllidaceae alkaloids viz. oxoassoanine (1b), anhydrolycorinone (1d), and other related structures. Interestingly, the method also works only in the presence of potassium tert-butoxide.

Neocuproine-KOtBu promoted intramolecular cross coupling to approach fused rings

Polycycles can be produced with different linkages (A, B = O, N, C, S) by constructing biaryl C-C bonds via neocuproine-KOtBu promoted cross coupling between C-Xs and C-Hs.

Novel Molecular Sensors for Saccharides Based on the Interaction of Boronic Acid and Amines: Saccharide Sensing in Neutral Water

The first known synthetic molecular colour sensor for saccharides is designed utilizing the boronic acid-amine interaction and visible colour changes were observed upon interaction with saccharides in neutral aqueous solutions.