34950-04-4

Usage

InChI:InChI=1/C13H11NO/c1-10-4-6-11(7-5-10)13(15)12-3-2-8-14-9-12/h2-9H,1H3

Upstream product

• 60573-68-4 3-pyridyllithium 
• 104-85-8 para-methylbenzonitrile 
• 10400-19-8 3-pyridinecarbonyl chloride 
• 108-88-3 toluene 
• 626-55-1 3-Bromopyridine 
• 201230-82-2 carbon monoxide 
• 5720-05-8 4-methylphenylboronic acid 
• 1120-90-7 3-iodopyridine 
• 1228460-48-7 C₁₇H₁₂N₄O₄ 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 13939-06-5 molybdenum hexacarbonyl 
• 500-22-1 3-pyridinecarboxaldehyde 
• 106-38-7 para-bromotoluene 
• 5142-75-6 tri(p-tolyl)bismuth 

Downstream Products

• 124009-73-0 α-(4-Methyl-phenyl)-α-trichlormethyl-3-pyridinmethanol 
• 1061206-51-6 (R)-pyridin-3-yl(p-tolyl)methanol 
• 1604834-24-3 C₂₃H₂₂N₂O 
• 150760-26-2 4-methyl-3-nitrophenyl-3-pyridylketone 

Relevant academic research and scientific papers

Palladium-Catalyzed Room-Temperature Acylative Suzuki Coupling of High-Order Aryl Borons with Carboxylic Acids

This note describes a dimethyl dicarbonate-assisted, Pd(OAc)2/PPh3-catalyzed acylative Suzuki coupling of carboxylic acids with diarylborinic acids or tetraarylboronates for practical and efficient synthesis of sterically undemanding aryl ketones at room temperature. More than just cost-effective alternatives to aryl boronic acids, diarylborinic acids and tetraarylboronates displayed higher reactivity in the acylative Suzuki coupling. A variety of alkyl aryl ketones, including those bearing a hydroxy, bromo, or carbonyl group, could be readily obtained in modest to excellent yields.

Phosphine-Free, Heterogeneous Palladium-Catalyzed Atom-Efficient Carbonylative Cross-Coupling of Triarylbismuths with Aryl Iodides: Synthesis of Biaryl Ketones

A novel and highly efficient heterogeneous palladium-catalyzed carbonylative cross-coupling of aryl iodides with triarylbismuths has been developed that proceeds smoothly at atmospheric CO pressure and provides a general and powerful tool for the preparation of various valuable biaryl ketones with high atom economy, good to excellent yield, and recyclability of the catalyst. The reaction is the first example of Pd-catalyzed carbonylative cross-coupling for the construction of biaryl ketones using triarylbismuths as substrates.

Expedient carbonylation of aryl halides in aqueous or neat condition

An expedient and versatile, microwave-assisted procedure for the carbonylation of aryl halides with boronic acids, alcohols or amines in water or under neat conditions has been developed. The reaction is catalyzed by fluorous, oxime-based palladacycle 1 that shows an excellent recyclable property and low levels of Pd leaching. To demonstrate the usefulness of the protocol, we applied it to the preparation of compounds of pharmaceutical interest, including a precursor of the reverse transcriptase inhibitor, niacin, benzocaine and butamben.

Efficient, recyclable and phosphine-free carbonylative Suzuki coupling reaction using immobilized palladium ion-containing ionic liquid: Synthesis of aryl ketones and heteroaryl ketones

The carbonylative Suzuki coupling reaction of aryl and heteroaryl iodides was studied by using immobilized palladium ion-containing ionic liquid (ImmPd-IL). The protocol was optimized with respect to various reaction parameters, applied to a wide variety of substituted aryl/heteroaryl iodides and various aryl/heteroaryl boronic acids with different steric and electronic properties, and afforded the corresponding products in good to excellent yield. This is an efficient, heterogeneous catalyst which avoids the use of phosphine ligands, and its reusability was tested in up to four consecutive cycles. The recycled catalyst was characterized by using XPS analysis.

Practical one-pot preparation of ketones from aryl and alkyl bromides with aldehydes and DIH via Grignard reagents

Various diaryl ketones, alkyl aryl ketones, and dialkyl ketones were efficiently prepared in good yields by the reactions of the Grignard reagents derived from aryl or alkyl bromides, followed by the reactions with aromatic or aliphatic aldehydes and the subsequent treatment with 1,3-diiodo-5,5- dimethylhydantoin and K2CO3, in a one-pot method. The same treatment of aromatic bromides bearing electron-withdrawing groups, such as ester, nitrile, ketone, and nitro groups with i-PrMgCl·LiCl or PhMgCl instead of Mg, also provided the corresponding diaryl and alkyl aryl ketones in good yields. The above methods are simple and practical transition-metal-free methods for the preparation of various diaryl ketones and alkyl aryl ketones bearing electron-rich aromatic groups and electron-deficient aromatic groups, as well as dialkyl ketones.

Facile preparation of aromatic ketones from aromatic bromides and arenes with aldehydes

Aromatic ketones were efficiently prepared in good yields by the reactions of aryl bromides with n-BuLi, followed by the reactions with aromatic aldehydes or aliphatic aldehydes and the subsequent treatment with molecular iodine and K2CO3, in a one-pot method. The same treatment of arenes, instead of aromatic bromides, also provided the corresponding aromatic ketones in good yields. Using these methods, various diaryl ketones and alkyl aryl ketones bearing electron-rich aromatics and electron-deficient aromatics could be prepared efficiently by a simple, transition-metal-free, and therefore environmentally benign experimental procedure.

Easy-to-execute carbonylative arylation of aryl halides using molybdenum hexacarbonyl: Efficient synthesis of unsymmetrical diaryl ketones

A versatile procedure for the synthesis of unsymmetrical diaryl ketones through a palladium-catalyzed carbonylative arylation of iodoarenes through easy-to-handle molybdenum hexacarbonyl as a condensed source of carbon monoxide is described. This method provides an efficient route to a wide variety of substituted diaryl ketones without direct use of high-pressure carbon monoxide. Copyright

Ligand-free Pd-catalyzed carbonylative cross-coupling reactions under atmospheric pressure of carbon monoxide: Synthesis of aryl ketones and heteroaromatic ketones

The carbonylative Suzuki cross-coupling reactions of boronic acids with aryl iodides catalyzed by Pd2(dba)3 as a ligand-free catalyst under atmospheric pressure of carbon monoxide has been firstly developed. Under mild reaction conditions, a broad range of aryl/heteroaryl iodides and aryl/heteroaryl boronic acids were selectively coupled to afford the corresponding diaryl ketones in good to excellent yields at low catalyst loadings (0.05 to 2 mol-%). Moreover, the catalyst can also be recycled. The carbonylative Suzuki cross-coupling reactions of boronic acids with aryl iodides catalyzed by Pd2(dba)3 as a ligand-free catalyst under an atmosphere of carbon monoxide has been developed. A broad range of aryl/heteroaryl iodides and aryl/heteroaryl boronic acids were selectively coupled to afford the corresponding diaryl ketones in good to excellent yields. The catalyst can also be recycled.

Phosphane-free palladium-catalyzed carbonylative suzuki coupling reaction of aryl and heteroaryl iodides

The carbonylative cross-coupling reaction of an arylboronic acid with an aryl iodide and a heteroaryl iodide to give unsymmetrical biaryl ketones was carried out by using Pd(tmhd)2/Pd (OAc)2 as a phosphane-free catalyst. Various aryl and heteroaryl iodides with different arylboronic acid derivatives provided, good, to excellent yields of the desired products under optimized reaction conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009.