80772-85-6

Upstream product

• 95-46-5 2-methylphenyl bromide 
• 1201921-86-9 C₁₃H₂₁NO₂ 
• 694-59-7 pyridine N-oxide 
• 552-45-4 1-chloromethyl-2-methylbenzene 
• 36995-45-6 2-[(2-methylphenyl)methyl]pyridine 
• 941279-81-8 2,4-dimethyl-3-(pyridin-2-ylmethyl)pentan-3-ol 
• 109-06-8 α-picoline 
• 95-47-6 o-xylene 
• 931-19-1 2-methylpyridine N-oxide 

Downstream Products

• 260-36-6 1-azaanthracene 
• 36995-45-6 2-[(2-methylphenyl)methyl]pyridine 
• 1015758-88-9 2-(2-methylbenzyl)-6-p-tolylpyridine 1-oxide 

Relevant academic research and scientific papers

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.

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.

Palladium-catalyzed benzylic cross-couplings of pyridine N-oxides

Palladium-catalyzed C-H couplings (CSP3-C SP2) of pyridine N-oxides with benzyl chloride derivatives is reported. It provides a novel and easy process for the synthesis of 2-benzylpyridine derivatives through benzylic cross-couplings of pyridine N-oxides. Georg Thieme Verlag Stuttgart · New York.

Catalyst and base controlled site-selective sp2 and sp3 direct arylation of azine N-oxides

Site-selective direct arylation of both sp2 and sp3 sites on azine N-oxide substrates is described. The arylation reactions are carried out in either a divergent manner or a sequential manner. The sp3 arylation reaction is applied to the synthesis of the natural products, papaverine and crykonisine, and a rationale for low reactivity of electron-deficient aryl halides is provided. Mechanistic investigations point toward the intimate involvement of the base in the mechanism of these reactions.