1131-61-9

Usage

Uses

Used in Catalyst Applications:
4-Phenylpyridine-N-oxide is used as a catalyst for various chemical reactions, such as halogen bonding and enantioselective epoxidation of non-selective alkenes, leading to higher catalytic activity. This enhances the efficiency and selectivity of these reactions, making it a valuable component in the synthesis of various compounds.
Used in Chemical Synthesis Studies:
4-Phenylpyridine-N-oxide may also be utilized in chemical synthesis studies, where its unique properties can contribute to the development of new synthetic pathways and the creation of novel compounds with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Phenylpyridine-N-oxide can be used as a key intermediate or building block in the synthesis of various drugs, taking advantage of its reactivity and structural features to design and develop new therapeutic agents.
Used in Material Science:
4-Phenylpyridine-N-oxide's unique properties may also find applications in material science, where it could be used to develop new materials with specific characteristics, such as improved optical, electronic, or mechanical properties, depending on the desired application.

InChI:InChI=1/C11H9NO/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H

Upstream product

• 939-23-1 p-phenylpyridine 
• 1121-76-2 4-chloropyridine N-oxide 
• 98-80-6 phenylboronic acid 
• 100-58-3 phenylmagnesium bromide 
• 75-57-0 tetramethlyammonium chloride 
• 3535-75-9 4-aminopyridine-1-oxide 
• 71-43-2 benzene 

Downstream Products

• 92929-30-1 4-(3-nitrophenyl)pyridine 1-oxide 
• 92929-31-2 4-(4-nitrophenyl)pyridine 1-oxide 
• 26274-35-1 2,4-diphenylpyridine 
• 939-23-1 p-phenylpyridine 
• 70197-13-6 methyltrioxorhenium(VII) 
• 19006-81-6 4-phenylpyridin-2-ol 
• 1123265-02-0 C₁₁H₉NO*C₆₀H₇₂N₈O₄ 
• 1123264-92-5 C₁₁H₉NO*C₆₀H₆₀N₄O₁₂ 
• 1123264-99-2 C₁₁H₉NO*C₅₆H₅₂N₄O₁₂ 
• 1228437-35-1 2-(4-methoxyphenyl)-4-phenylpyridine N-oxide 
• 108702-79-0 diethyl 4-phenylpyridin-2-ylphosphonate 
• 6153-92-0 4,4'-diphenyl-2,2'-bipyridine 

Relevant academic research and scientific papers

Visible-Light-Induced ortho-Selective Migration on Pyridyl Ring: Trifluoromethylative Pyridylation of Unactivated Alkenes

The photocatalyzed ortho-selective migration on a pyridyl ring has been achieved for the site-selective trifluoromethylative pyridylation of unactivated alkenes. The overall process is initiated by the selective addition of a CF3 radical to the alkene to provide a nucleophilic alkyl radical intermediate, which enables an intramolecular endo addition exclusively to the ortho-position of the pyridinium salt. Both secondary and tertiary alkyl radicals are well-suited for addition to the C2-position of pyridinium salts to ultimately provide synthetically valuable C2-fluoroalkyl functionalized pyridines. Moreover, the method was successfully applied to the reaction with P-centered radicals. The utility of this transformation was further demonstrated by the late-stage functionalization of complex bioactive molecules.

Deoxygenative Amination of Azine-N-oxides with Acyl Azides via [3 + 2] Cycloaddition

A transition-metal-free deoxygenative C-H amination reaction of azine-N-oxides with acyl azides is described. The initial formation of an isocyanate from the starting acyl azide via a Curtius rearrangement can trigger a [3 + 2] dipolar cycloaddition of polar N-oxide fragments to generate the aminated azine derivative. The applicability of this method is highlighted by the late-stage and sequential amination reactions of complex bioactive compounds, including quinidine and fasudil. Moreover, the direct transformation of aminated azines into various bioactive N-heterocycles illustrates the significance of this newly developed protocol.

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.

Electrochemical Deoxygenation of N-Heteroaromatic N -Oxides

An electrochemical method for the deoxygenation of N-heteroaromatic N -oxide to give the corresponding N-heteroaromatics has been developed. Several classes of N-heterocycles such as pyridine, quinoline, isoquinoline, and phenanthridine are tolerated. The electrochemical reactions proceed efficiently in aqueous solution without the need for transition-metal catalysts and waste-generating reducing reagents.

Pd-Catalyzed Direct C-H Alkenylation and Allylation of Azine N -Oxides

A Pd-catalyzed direct C2-alkenylation of azine N-oxides with allyl acetate is disclosed. The products are formed through an allylation/isomerization cascade process. The use of a tri-tert-butylphosphonium salt as the ligand precursor and KF is mandatory for optimal yields. When cinnamyl acetate is used, the same catalytic system promotes C2-cinnamylation of the azine N-oxide without subsequent isomerization. A mechanism is proposed on the basis of experimental studies and DFT calculations.

Visible Light-Mediated Decarboxylative Alkylation of Pharmaceutically Relevant Heterocycles

A net redox-neutral method for the decarboxylative alkylation of heteroarenes using photoredox catalysis is reported. Additionally, this method features the use of simple, commercially available carboxylic acid derivatives as alkylating agents, enabling the facile alkylation of a variety of biologically relevant heterocyclic scaffolds under mild conditions.

Nickel-catalyzed C–H trifluoromethylation of pyridine N-oxides with Togni's reagent

The first nickel-catalyzed C–H trifluoromethylation of pyridine N-oxides with Togni's reagent has been achieved. Trifluoromethylation proceeds smoothly under mild conditions with moderate functional group compatibility. Notable advantages of this method include the using of low cost of nickel catalyst, and its simple convenient operation.

Iodine/TBHP-Promoted One-Pot Deoxygenation and Direct 2-Sulfonylation of Quinoline N-Oxides with Sodium Sulfinates: Facile and Regioselective Synthesis of 2-Sulfonylquinolines

A highly efficient iodine/TBHP-mediated one-pot deoxygenative and regioselective 2-sulfonylation of quinoline N-oxides with sodium sulfinate salts has been developed. This metal-, base-, and phosphorus-free protocol employs readily accessible and easy-to-handle reagents and can be conveniently carried out at room temperature under mild conditions, providing an alternative access to a series of 2-sulfonylquinolines and other related heteroaryl sulfone products in moderate-to-excellent yields within a short reaction time.

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.

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.