1173294-92-2

Upstream product

• 1008-89-5 2-phenylpyridine 
• 1122-91-4 4-bromo-benzaldehyde 
• 7099-87-8 4-bromophenylglyoxylic acid 
• 106-38-7 para-bromotoluene 
• 586-76-5 4-Bromobenzoic acid 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 6940-50-7 4-bromo-DL-mandelic acid 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 623-00-7 4-bromobenzenecarbonitrile 
• 98-80-6 phenylboronic acid 
• 109-04-6 2-bromo-pyridine 
• 99-90-1 para-bromoacetophenone 
• 56472-73-2 C₉H₈BrNO₂ 
• 10342-83-3 4'-Bromopropiophenone 

Downstream Products

• 1404120-32-6 (4-bromophenyl)(2-(pyridin-2-yl)phenyl)methanol 

Relevant academic research and scientific papers

An Approach to Nonsymmetric Bis(tertiary phosphine oxides) Comprising Heterocyclic Fragments via the Pd-Catalyzed Phosphorylation

Nonsymmetric tertiary phosphine oxides with different five- and six-membered heterocyclic fragments such as pyridine, 2,2′-bipyridine, 1,10-phenantroline, quinoline, imidazole, and thiazole were synthesized in good yields via the successive introduction of phosphine oxide groups into the initial dihalogenated heterocycles by means of Pd-catalyzed phosphorylation reaction. The synthesis of pyridine-type compounds is hindered by competing double coupling, while for five-membered heterocycles the principal difficulty is the dehalogenation. Both side processes were successfully suppressed by the use of an excess of a dihalide (which can be easily recovered during the product purification step), proper phosphine ligand for palladium, and nonpolar solvent such as toluene.

Acylation of Arenes with Aldehydes through Dual C-H Activations by Merging Photocatalysis and Palladium Catalysis

An acylation of arenes with aldehydes through dual C-H activations at room temperature is reported. The acylation was initiated by phenanthraquinone-catalyzed hydrogen atom transfer from aldehyde under visible light irradiation. The aldehyde-derived acyl

Dual photoredox/palladium-catalyzed C-H acylation of 2-arylpyridines with oxime esters

An unprecedented dual photoredox/palladium-catalyzed iminyl-radical-mediated C-C bond cleavage and directed ortho C-H acylation of 2-arylpyridines by using oxime esters is described. Oxime esters can serve as efficient acyl sources through formation of the corresponding acyl radicals by photoredox-catalyzed iminyl-radical-mediated C-C bond cleavage. This redox-neutral protocol features excellent regioselectivity, a broad substrate scope, and good functional-group tolerance with respect to both components, giving a broad range of aryl ketones with generally good yields.

Ruthenium-Catalyzed Carbonylative Coupling of Anilines with Organoboranes by the Cleavage of Neutral Aryl C-N Bond

Herein, we report the first ruthenium-catalyzed Suzuki-type carbonylative reaction of electronically neutral anilines via C(aryl)-N bond cleavage. Without any ligand and base, diaryl ketones can be obtained in moderate to high yields by using Ru3/su

I-Pr2NMgCl·LiCl Enables the Synthesis of Ketones by Direct Addition of Grignard Reagents to Carboxylate Anions

The direct preparation of ketones from carboxylate anions is greatly limited by the required use of organolithium reagents or activated acyl sources that need to be independently prepared. Herein, a specific magnesium amide additive is used to activate and control the addition of more tolerant Grignard reagents to carboxylate anions. This strategy enables the modular synthesis of ketones from CO2 and the preparation of isotopically labeled pharmaceutical building blocks in a single operation.

Nickel-catalyzed regioselective C-H acylation of chelating arenes: A new catalytic system for C-C bond formation: Via a radical process and its mechanistic explorations

An unprecedented acylation at the ortho C-H bond of chelating arenes via the Ni(ii)-catalyzed cross dehydrogenative coupling strategy has been developed here. This new procedure exhibits excellent regioselectivity and good functional group tolerance. This discovery could be of great importance for the C-H acylation reactions of chelating arenes without any extraneous directing group and for the application of nickel-catalyzed C-H activation. Mechanistic investigations into the reaction process are also described.

Use of Cyclopropane as C1 Synthetic Unit by Directed Retro-Cyclopropanation with Ethylene Release

Cyclopropanation of alkenes is a well-established textbook reaction for the synthesis of cyclopropanes, where a "high-energy" carbene species is exploited to drive the reaction forward. However, little attention has been focused toward molecular transformations involving the reverse reaction, retro-cyclopropanation (RC). This is because of difficulties associated with both cleaving the two geminal C-C single bonds and exploiting the generated carbenes for further transformations in an efficient and selective manner. Here, we report that a molybdenum-based catalytic system overcomes the above challenges and effects the RC of cyclopropanes bearing a pyridyl group with the release of ethylene (alkene) and the subsequent intramolecular cyclization leading to pyrido[2,1-a]isoindoles. The reaction allows for the uncommon use of cyclopropanes as C1 synthetic units in contrast to most conventional reactions in which cyclopropanes are used as C3 synthetic units. We anticipate that this new strategy will pave the way for C1 cyclopropane chemistry.

Palladium-catalyzed decarboxylative, decarbonylative and dehydrogenative C(sp2)-H acylation at room temperature

Over the past few decades, an impressive array of C-H activation methodology has been developed for organic synthesis. However, due to the inherent inertness of the C-H bonds (e.g. ～110 kcal mol-1 for the cleavage of C(aryl)-H bonds) harsh reaction conditions have been realized to overcome high energetic transition states resulting in a limited substrate scope and functional group tolerance. Therefore, the development of mild C-H functionalization protocols is in high demand to exploit the full potential of the C-H activation strategy in the synthesis of a complex molecular framework. Although, electron-rich substrates undergo electrophilic metalation under relatively mild conditions, electron-deficient substrates proceed through a rate-limiting C-H insertion under forcing conditions at high temperature. In addition, a stoichiometric amount of toxic silver salt is frequently used in palladium catalysis to facilitate the C-H activation process which is not acceptable from the environmental and industrial standpoint. We report herein, a Pd(ii)-catalyzed decarboxylative C-H acylation of 2-arylpyridines with α-ketocarboxylic acids under mild conditions. The present protocol does not require stoichiometric silver(i) salts as additives and proceeds smoothly at ambient temperature. A novel decarbonylative C-H acylation reaction has also been accomplished using aryl glyoxals as acyl surrogates. Finally, a practical C-H acylation via a dehydrogenative pathway has been demonstrated using commercially available benzaldehydes and aqueous hydroperoxides. We also disclose that acetonitrile solvent is optimal for the acylation reaction at room temperature and has a prominent role in the reaction outcome. Control experiments suggest that the acylation reaction via decarboxylative, decarbonylative and dehydrogenative proceeds through a radical pathway. Thus we disclose a practical protocol for the sp2 C-H acylation reaction.

Replacing Pd(OAc)2 with supported palladium nanoparticles in ortho-directed CDC reactions of alkylbenzenes

Supported palladium nanoparticles are used as efficient catalysts for the synthesis of aromatic ketones via cross dehydrogenative coupling reactions of 2-arylpyridines with alkylbenzenes. The catalyst can be reused for five cycles without significantly losing activity. Mechanism research showed that alkylbenzenes were oxidized to their corresponding aldehydes and subsequently coupled with 2-arylpyridines to generate aryl ketones through a Pd0/PdII/PdIV catalytic cycle.

Palladium-Catalyzed Oxidative Direct ortho-C-H Acylation of Arenes with Aldehydes under Aqueous Conditions

Palladium-catalyzed ortho-acylation of arenes with aldehydes in the presence of tert-butyl hydroperoxide (TBHP) as the oxidant under aqueous conditions has been demonstrated. The acylation reaction exhibits excellent regioselectivity and wide functional g