20531-86-6

Upstream product

• 101-82-6 2-Benzylpyridine 
• 108-86-1 bromobenzene 
• 1201921-98-3 C₁₄H₁₅NO₂ 
• 30643-33-5 trans-bromo(phenyl)bis(triphenylphosphine)palladium(II) 
• 1201921-86-9 C₁₃H₂₁NO₂ 
• 591-50-4 iodobenzene 
• 108-90-7 chlorobenzene 
• 694-59-7 pyridine N-oxide 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 6921-34-2 benzylmagnesium chloride 
• 109-09-1 2-chloropyridine 
• 108-88-3 toluene 
• 110-86-1 pyridine 

Downstream Products

• 20482-09-1 2-(4-nitro-benzyl)-pyridine-1-oxide 
• 93-98-1 N-phenyl benzoyl amide 
• 28830-48-0 α,α'-bis-(2-pyridyl)bibenzyl 
• 30914-88-6 2,2-dimethyl-4-keto-1,3-benzoxazine 
• 40473-17-4 2‐(chloro(phenyl)methyl)pyridine 
• 76809-16-0 2,2-Dimethyl-3-(phenyl-pyridin-2-yl-methyl)-2,3-dihydro-benzo[e][1,3]oxazin-4-one 
• 76809-26-2 3-(2-Benzyl-pyridin-3-yl)-2,2-dimethyl-2,3-dihydro-benzo[e][1,3]oxazin-4-one 
• 76809-33-1 3-(6-Benzyl-pyridin-3-yl)-2,2-dimethyl-2,3-dihydro-benzo[e][1,3]oxazin-4-one 
• 101-82-6 2-Benzylpyridine 
• 245-43-2 benzo<2,3>indolizine 
• 620-87-1 2-(4-nitrobenzyl)pyridine 
• 57963-09-4 6-benzylpyridin-2-amine 
• 139478-84-5 6-benzylpicolinonitrile 
• 80205-36-3 [Rh(COD)(2-BzPyO)2]ClO₄ 

Relevant academic research and scientific papers

Switchable Oxidative Reactions of N-allyl-2-Aminophenols: Palladium-Catalyzed Alkoxyacyloxylation vs an Intramolecular Diels-Alder Reaction

The Pd(II)-catalyzed reaction of N-allyl-2-aminophenols in the presence of PhI(OCOR)2 as the oxidant resulted in an alkoxyacyloxylation process, with the formation of functionalized dihydro-1,4-benzoxazines. The reaction performed in the absence of pallad

Acylation of 2-benzylpyridine N-oxides and subsequent in situ [3,3]-sigamatropic rearrangement reaction

An effective method for the acylation of 2-benzylpyridine N-oxides and their fast in situ [3,3]-sigmatropic rearrangement was reported. This transformation has a wide substrate scope under mild conditions, giving moderate to excellent yields. The application for the synthesis of chiral phenyl-2-pyridylmethanol products was briefly explored. Furthermore, an interesting example of tandem substitution and in situ [3,3]-sigamatropic rearrangement of 2-benzylpyridine N-oxide with benzenecarboximidoyl chloride was reported.

Visible-Light-Mediated C-H Alkylation of Pyridine Derivatives

We report herein a visible-light-mediated C-H alkylation of pyridine derivatives that proceeds by simple combination of a large variety of N-alkoxypyridinium ions with alkanes in the presence of 2 mol % of fac-Ir(ppy)3 under blue illumination. The mild reaction conditions together with the high group functional tolerance make of this process a useful synthetic platform for the construction of structurally strained heterocycles. Detailed mechanistic investigations, including density functional theory calculations and quantum yield measurement, allowed us to understand factors controlling the reactivity and the selectivity of the reaction.

The M?CPbA?NH3(G) system: A safe and scalable alternative for the manufacture of (substituted) pyridine and quinoline N?oxides?

An improved, safe, and scalable isolation process for (substituted) pyridine and quinoline N-oxides in quantitative yields along with high purities using the m-CPBA?NH3(g) system is described. The safety was assessed by reaction calorimetry and differential scanning calorimetry studies for possible hazards during the conversion and isolation steps. Careful interpretation of the data substantiated the safety and scalability. The process flow is simplified to meet the industrial requirements of safety, cost-effectiveness, and utility minimization. The reaction was safely demonstrated at a 2.5 kg scale.

Visible-Light-Promoted Copper-Catalyzed Regioselective Benzylation of Pyridine N-Oxides versus Thermal Acylation Reaction with Toluene Derivatives

Copper-catalyzed visible light mediated direct C–H bond benzylation of pyridine N-oxides with toluene derivatives was accomplished by recent developments in photochemical carbon–carbon bond formation through a photo-induced bond-dissociation strategy. Thi

Enantioselective Pd(II)-Catalyzed Intramolecular Oxidative 6- endo Aminoacetoxylation of Unactivated Alkenes

A novel asymmetric 6-endo aminoacetoxylation of unactivated alkenes by palladium catalysis, which yields chiral β-acetoxylated piperidines with excellent chemo-, regio- and enantioselectivities under very mild reaction conditions, has been established herein by employing a new designed pyridine-oxazoline (Pyox) ligand. Importantly, introducing a sterically bulky group into the C-6 position of Pyox is crucial to enhance the reactivity of the aminoacetoxylation of alkenes.

Benzylation of heterocyclic N-oxides via direct oxidative cross-dehydrogenative coupling with toluene derivatives

A novel cross-dehydrogenative coupling (CDC) of heterocyclic N-oxides with toluene derivatives has been discussed, allowing for the facile synthesis of a broad range of structurally diverse C1-benzyl quinoline N-oxides, isoquinoline N-oxides and pyridine N-oxides, including two methylated quinoline N-oxides in particular. This protocol not only extends the application of toluenes in synthetic organic chemistry, but also offers an alternative method to prepare benzylated heterocyclic N-oxides without any metal involved, which is important in medicinal chemistry.

Solvent- and halide-free synthesis of pyridine-2-yl substituted ureas through facile C-H functionalization of pyridine: N -oxides

A novel solvent- and halide-free atom-economical synthesis of practically useful pyridine-2-yl substituted ureas utilizes easily accessible or commercially available pyridine N-oxides (PyO) and dialkylcyanamides. The observed C-H functionalization of PyO is suitable for the good-to-high yielding synthesis of a wide range of pyridine-2-yl substituted ureas featuring electron donating and electron withdrawing, sensitive, or even fugitive functional groups at any position of the pyridine ring (63-92%; 19 examples). In the cases of 3-substituted PyO, the C-H functionalization occurs regioselectively providing a route for facile generation of ureas bearing a 5-substituted pyridine-2-yl moiety.

The microwave-assisted ortho-alkylation of azine N-oxides with N-tosylhydrazones catalyzed by copper(i) iodide

A copper catalyzed regioselective cross-coupling of N-tosylhydrazones with azine N-oxides to yield ortho-alkylated products in moderate to good yields is reported. The reaction is facilitated by microwave, takes place without any ligand, and uses inexpensive copper(i) iodide as the catalyst.

Palladium-catalyzed regioselective benzylation-annulation of pyridine N -oxides with toluene derivatives via multiple c-h bond activations: Benzylation versus arylation

A palladium-catalyzed cross-dehydrogenative coupling (CDC) reaction of pyridine N-oxides with toluenes has been developed that operates under mild conditions. 2-Benzylpyridines can be obtained directly by this method via a CDC reaction between unactivated toluenes and pyridine N-oxides. In addition, azafluorene N-oxides, of value for future medicinal chemistry applications, can be obtained successfully by this procedure via four tandem C-H bond activations.