100709-10-2

Upstream product

• 614-30-2 N-methyl-N-phenyl-benzenemethanamine 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 20244-61-5 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one 
• 5467-74-3 4-Bromophenylboronic acid 
• 183677-71-6 2-(4-bromophenyl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 947515-73-3 (4-bromophenyl)[2-(hydroxymethyl)phenyl]dimethylsilane 
• 6911-87-1 4-bromo-N-methylaniline 
• 87100-28-5 pinacol benzylboronate 
• 65-85-0 benzoic acid 
• 64-18-6 formic acid 
• 100-52-7 benzaldehyde 
• 106-40-1 4-bromo-aniline 
• 100-39-0 benzyl bromide 

Downstream Products

• 19689-37-3 N-benzyl-4-bromo-N-methyl-aniline-N-oxide 
• 1280078-91-2 C₂₁H₁₇FN₂S 
• 1280078-92-3 C₂₂H₂₀N₂S 
• 1280078-93-4 C₂₁H₁₇N₃O₂S 
• 1280078-66-1 C₁₈H₂₃BN₂O₂ 
• 19689-47-5 O-benzyl-N-(4-bromo-phenyl)-N-methyl-hydroxylamine 
• 33046-25-2 4-bromo-N,N,N-trimethylbenzenaminium iodide 
• 93947-48-9 2-methyl-1,1-bis-(4-methylamino-phenyl)-propan-2-ol 

Relevant academic research and scientific papers

One-Pot Transfer Hydrogenation Reductive Amination of Aldehydes and Ketones by Iridium Complexes “on Water”

An efficient and practical one-pot transfer hydrogenation reductive amination of aldehydes and ketones with amines has been developed by using iridium complexes as catalysts and formic acid as hydrogen source in aqueous solution, providing an environmentally friendly methodology for the construction of a wide range of functionalized amine compounds in excellent yields (≈ 80 %-95 %). This effective methodology can be scaled up to gram scale with 0.1 mol-% catalyst loading and also be employed in the synthesis of medical substances such as Meclizine.

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.

Electrochemical Regioselective Bromination of Electron-Rich Aromatic Rings Using n Bu 4 NBr

Electrochemical regioselective bromination of electron-rich aromatic rings using stoichiometric tetrabutylammonium bromide (n Bu 4 NBr) has been accomplished under mild conditions. This protocol provides an environmentally friendly and simple way for the construction of C-Br bond in moderate to high yields with wide functional group tolerance.

Air-tolerant direct reductive N-methylation of amines using formic acid via simple inorganic base catalysis

The construction of N-methyl amine moieties is an important reaction that has found numerous applications. Development of new methylation agents that are more environmentally benign than classical agents, such as iodomethane and methyl sulfate, is still highly desirable. Herein, we report a convenient protocol for direct reductive N-methylation of amines using formic acid as the methylation agent via simple inorganic base catalysis. The present protocol operates under transition-metal-free and air-tolerant conditions. Both the catalyst, K2HPO4, and the reductant, polymethylhydrosiloxane (PMHS), are cheap and easily separable from the crude reaction product mixture. Mechanistic investigations suggest that the reaction occur through the formation of an acetal intermediate followed by the C–N bond formation.

Method for alkylating amine

The invention provides a method for alkylating amine. The method comprises the following steps: adding primary amine or secondary amine, carboxylic acid, a reductant, a catalyst and a solvent into a reactor, reacting at 100-120 DEG C to obtain an alkylate of primary amine or secondary amine, wherein the reductant is phenylsilane, and the catalyst is carbonate. In the method provided by the invention, carbonate is used as a catalyst, carboxylic acid is used as a substrate, phenylsilane is used as a reductant, primary amine or secondary amine is converted into the corresponding alkylate in a butyl ether solvent. The method of the invention has the advantages of low cost, low toxicity, and high yield.

Copper-catalyzed N- and O-alkylation of amines and phenols using alkylborane reagents

By the reaction of amines with alkylborane reagents in the presence of a catalytic amount of copper(II) acetate Cu(OAc)2 and di-tert-butyl peroxide, a cross-coupling reaction proceeded and alkylated amines were obtained in good to excellent yields. Phenols are also applicable for this reaction, and the corresponding alkyl aryl ethers were produced.

Copper-catalyzed electrophilic amination of arylsilanes with hydroxylamines

A copper-catalyzed electrophilic amination of aryl[(2-hydroxymethyl)phenyl] dimethylsilanes with O-acylated hydroxylamines has been developed to afford the corresponding anilines in good yields. The catalytic reaction proceeds very smoothly under mild conditions and tolerates a wide range of functional groups.

Copper-catalyzed amination of arylboronates with N,N-dialkylhydroxylamines

A tolerant coupling: The title reaction has been developed to deliver arylamines (see scheme; Bz=benzoyl, dppbz=1,2-bis(diphenylphosphino)benzene). The catalysis is based on electrophilic, umpolung amination and enables the use of secondary acyclic amines. Various functional groups are tolerated, thus opening up a new substrate class for the Chan-Lam-type coupling.

Oxidative bromination of aromatic compounds using O-iodoxybenzoic acid with tetraethylammonium bromide

A mild and selective procedure for the bromination of activated arenes using o-iodoxybenzoic acid and tetraethylammonium bromide is presented. The reactions were carried out at room temperature and gave moderate to excellent yields. Copyright Taylor & Francis Group, LLC.