20173-75-5

Upstream product

• 5683-33-0 2-(Dimethylamino)pyridine 
• 100-44-7 benzyl chloride 
• 6935-27-9 N-benzylpyridin-2-amine 
• 74-88-4 methyl iodide 
• 109-04-6 2-bromo-pyridine 
• 103-67-3 benzyl-methyl-amine 
• 109-09-1 2-chloropyridine 
• 372-48-5 2-fluoropyridine 
• 4597-87-9 2-(N-methylamino)pyridine 
• 100-52-7 benzaldehyde 
• 1628-89-3 2-methoxypyridine 
• 15103-48-7 pyridine-2-sulfonic acid 
• 78-92-2 iso-butanol 
• 67-56-1 methanol 

Downstream Products

• 4597-87-9 2-(N-methylamino)pyridine 
• 127980-61-4 N-(2-pyridyl)-N-methyl-α-phenyl(n-propyl)amine 

Relevant academic research and scientific papers

Aminoborohydrides 15. The First Mild and Efficient Method for Generating 2-(Dialkylamino)-pyridines from 2-Fluoropyridine

(Matrix presented) Lithium aminoborohydride (LAB) reagents promote the amination of 2-fluoropyridine under mild reaction conditions, providing 2-(dialkylamino)-pyridines in excellent yield and purity. Treatment of 2-fluoropyridine with 1.1 equiv of lithiu

Rapid Amination of Methoxy Pyridines with Aliphatic Amines

A n-BuLi triggered practical amination protocol of methoxy pyridine derivatives with aliphatic amines was developed. The reaction could finish in 30 min for primary amines and 10 min for secondary amines. The amination is further highlighted by its excell

Synthesis and characterization of an isopropylBippyPhos precatalyst

A review of our high throughput reaction screening data revealed that BippyPhos was frequently associated with successful outcomes in Buchwald – Hartwig amination reactions. A barrier to the wider use of this ligand, particularly among those performing sm

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.

Metal-Free Synthesis of Heteroaryl Amines or Their Hydrochlorides via an External-Base-Free and Solvent-Free C-N Coupling Protocol

Herein, a metal-free and solvent-free protocol was developed for the C-N coupling of heteroaryl halides and amines, which afforded numerous heteroaryl amines or their hydrochlorides without any external base. Further investigations elucidated that the basicity of amines and specific interactions derived from the X-ray crystallography analysis of 3j′·HCl played pivotal roles in the reactions. Moreover, this protocol was scalable to gram scales and applicable to drug molecules, which demonstrated its practical value for further applications.

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.

Nickel-Catalyzed Intramolecular Desulfitative C - N Coupling: A Synthesis of Aromatic Amines

A nickel-catalyzed intramolecular C - N coupling reaction via SO2 extrusion is presented. The use of a catalytic amount of BPh3 allows the transformation to take place under much milder conditions (60 °C) than previously reported C - N coupling reactions by CO or CO2 extrusion (160-180 °C). In addition, this method displays good functional group tolerance and versatility, as it can be applied to the synthesis of dialkyl aryl amines, alkyl diaryl amines, and triaryl amines. The robustness of the desulfitative C - N coupling is demonstrated by three high-yielding gram-scale reactions.

Amination of 2-Pyridinesulfonic and 8-Quinolinesulfonic Acids with Magnesium Amides

The amination of 2-pyridine- and 8-quinolinesulfonic acids using magnesium amides of the type R2NMgCl·LiCl is reported. Thus, several cyclic and acyclic amines were converted into the corresponding amides using iPrMgCl·LiCl, which reacted readily with sulfonic acids to produce aminopyridines and aminoquinolines. Various amines which are attractive in drug chemistry were suitable for this transformation.

The synthesis of planar chiral pseudo-gem aminophosphine pre-ligands based on [2.2]paracyclophane

The synthesis of three planar chiral pseudo-gem disubstituted [2.2]paracyclophane-derived P,N-pre-ligands is reported along with preliminary results of their activity in the amination of aryl bromides and chlorides. The pseudo-gem aminophosphines were capable of mediating the coupling reaction at a loading of 1 mol%.