59576-38-4

Upstream product

• 5093-70-9 4-bromo-2,6-dimethylpyridine 
• 98-88-4 benzoyl chloride 
• 93-97-0 benzoic acid anhydride 
• 100-58-3 phenylmagnesium bromide 
• 39965-81-6 2,6-dimethylisonicotinonitrile 
• 611-73-4 Benzoylformic acid 
• 81128-26-9 2,6-dimethyl-4-(trimethyl-stannyl)pyridine 
• 857435-75-7 (2,6-dimethyl-[4]pyridyl)-phenyl-acetonitrile 

Downstream Products

• 116600-66-9 (2,6-dimethyl-1-oxy-[4]pyridyl)-phenyl ketone 

Relevant academic research and scientific papers

Physical Organic Approach to Persistent, Cyclable, Low-Potential Electrolytes for Flow Battery Applications

The deployment of nonaqueous redox flow batteries for grid-scale energy storage has been impeded by a lack of electrolytes that undergo redox events at as low (anolyte) or high (catholyte) potentials as possible while exhibiting the stability and cycling lifetimes necessary for a battery device. Herein, we report a new approach to electrolyte design that uses physical organic tools for the predictive targeting of electrolytes that possess this combination of properties. We apply this approach to the identification of a new pyridinium-based anolyte that undergoes 1e- electrochemical charge-discharge cycling at low potential (?1.21 V vs Fc/Fc+) to a 95% state-of-charge without detectable capacity loss after 200 cycles.

DECARBOXYLATIVE CROSS-COUPLING AND APPLICATIONS THEREOF

Methods described herein enable the production of numerous molecular species through decarboxylative cross-coupling via use of photoredox and transition metal catalysts. For example, methods described herein enable the production of numerous molecular species through decarboxylative cross-coupling via use of photoredox and transition metal catalysts. A method described herein, in some embodiments, comprises providing a reaction mixture including a photoredox catalyst, a transition metal catalyst, a coupling partner and a substrate having a carboxyl group. The reaction mixture is irradiated with a radiation source resulting in cross-coupling of the substrate and coupling partner via a mechanism including decarboxylation, wherein the coupling partner is selected from the group consisting of a substituted aromatic compound and a substituted aliphatic compound.

Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo Acids

The direct decarboxylative arylation of α-oxo acids has been achieved by synergistic visible-light-mediated photoredox and nickel catalysis. This method offers rapid entry to aryl and alkyl ketone architectures from simple α-oxo acid precursors via an acyl radical intermediate. Significant substrate scope is observed with respect to both the oxo acid and arene coupling partners. This mild decarboxylative arylation can also be utilized to efficiently access medicinal agents, as demonstrated by the rapid synthesis of fenofibrate. The direct decarboxylative arylation of α-oxo acids has been achieved by synergistic visible-light-mediated photoredox and nickel catalysis. This method offers rapid entry to aryl and alkyl ketone architectures from simple α-oxo acid precursors via an acyl radical intermediate. Significant substrate scope is observed with respect to both the oxo acid and arene coupling partners.

Preparation of ?-Deficient Heteroarylzinc Halides by Oxidative Addition of Active Zinc and Its Palladium-Catalyzed Reaction

The oxidative addition of active zinc to iodo- and bromo-substituted ?-deficient heteroarenes such as pyridine, pyrimidine, and quinoline gave the corresponding heteroarylzinc halides which were transformed to the arylated and benzoylated derivatives by palladium-catalyzed reaction.

Studies on Organometallic Compounds. III. Reaction of Trimethylstannylazines with Acyl Chlorides. A Novel C-C Bond Formation of Pyridine Nuclei

Introduction of an acyl group at the α-, β-, and γ-positions of pyridine nuclei was accomplished. 2-Trimethylstannyl-pyridine and -quinoline and 1-trimethylstannylisoquinoline directly reacted with various acyl chlorides to give the corresponding 2-pyridyl, 2-quinolyl, and 1-isoquinolyl ketones, respectively.Reaction of 3-trimethylstannylpyridine, -quinoline, and -isoquinoline with acyl chlorides proceeded smoothly under catalysis by PdCl2 or PdCl2(PPh3)2 to afford the corresponding ketones in good yields.Similary, 4-pyridyl, -quinolyl, and -isoquinolyl ketones were prepared from corresponding 4-trimethylstannyl derivatives and acyl chlorides.Keywords--trimethylstannylazine; palladium-catalyzed reaction; acylation; palladium dichloride; dichlorobis(triphenylphosphine)palladium(II)

A SIMPLE METHOD FOR INTRODUCTION OF ACYL GROUPS INTO PYRIDINE NUCLEI VIA TRIMETHYLSTANNYL-PYRIDINES AND QUINOLINES.

The 2-trimethylstannyl (TMSn) derivatives of pyridine and quinoline were directly treated with acyl chlorides to afford the corresponding 2-acyl-pyridines and -quinolines in good yields.On the other hand, replacement of the 3- and 4-TMSn groups by acyl groups was satisfactorily achieved by catalysis of palladium compound such as PdCl2 or PdCl2(PPh3)2.