63506-58-1

Upstream product

• 529-28-2 4-iodoanisol 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 610-96-8 methyl chlorobenzoate 

Downstream Products

• 2005-10-9 6H-benzo[c]chromen-6-one 
• 182355-39-1 (2'-methoxy)biphenyl-2-yl acetic acid 

Relevant academic research and scientific papers

An aromatic heterocyclic compound and use thereof

The invention provides an aromatic heterocyclic compound. The compound is as shown in formula (1), wherein Y1 is an oxygen atom or a sulfur atom; Y2 is an oxygen atom, a sulfur atom, NR3 or CR1R2, wherein R1, R2 are respectively selected from one of a hydrogen atom, a methyl group, an ethyl group, a propyl group, a tert-butyl group and a phenyl group, and R3 is the hydrogen atom or the phenyl group; X11-X20 are respectively selected from a nitrogen atom or CR4, and at least one of the X11-X20 is a carbon atom which is linked to L1 through a single bond, wherein R4 is the hydrogen atom, a halogen atom or a cyano group; at least one of the X17-X20 is the nitrogen atom. According to the aromatic heterocyclic compound, the aromatic heterocyclic compound has a similar structure as a dibenzofuran derivative and a dibenzothiophene derivative, electron transport can be improved, high light, low voltage, high efficiency and long service life of an organic EL component can be achieved, and the aromatic heterocyclic compound can be extensively applied in an OLED luminescent device and a display device to be used as the host material of a luminescent layer.

Exploration of Biaryl Carboxylic Acids as Proton Shuttles for the Selective Functionalization of Indole C-H Bonds

A survey of diversely substituted 2-arylbenzoic acids were synthesized and tested for use as proton shuttle in the direct arylation of indoles with bromobenzenes. It was found that 3-ethoxy-2-phenylbenzoic acid gives superior yield and selectivity for this class of substrates.

A reusable heterogeneous catalyst without leaking palladium for highly-efficient Suzuki-Miyaura reaction in pure water under air

Herein, we report a heterogenous catalyst (Pd@FSM) by immobilization of a novel Pd2+ sensor as promoter over mesoporous silica. Pd@FSM with a high palladium loading of ca. 11 mg g-1 exhibited superior catalytic activity for Suzuki-Miyaura cross-couplings and a catalyst loading of 0.05 mol% is typically sufficient to achieve excellent reaction yields. Notably, the reaction is typically carried out in water without removing atmospheric oxygen. The catalyst is conveniently recycled and remains highly active even after being recycled 5 times. During this process, loss of palladium from the solid support of the catalyst is negligible. Furthermore, the catalyst can be stored in air for at least three months without loss of its catalytic activity. This work provides a new approach to developing heterogeneous palladium catalysts by combing materials and fluorescent sensors.

A mild robust generic protocol for the Suzuki reaction using an air stable catalyst

A mild but robust procedure has been developed as a first pass generic protocol for the Suzuki-Miyaura reaction. The protocol employs an air stable palladium pre-catalyst at low loading (1 mol %) in aqueous solvent mixtures at moderate temperature using potassium carbonate as base. Under these mild conditions, most aryl bromides will react with sterically and electronically demanding aryl boronic acids to give complete conversion to the product biphenyls in less than 1 h. Aryl chlorides are also fully converted in most cases either under identical conditions in 8-24 h, or in 2 h at elevated temperature. A further advantage of these mild conditions of moderate temperature, weak base and benign solvent is that sensitive functional groups and structural motifs are well tolerated. In addition, the lipophilic biphenyl products are readily isolated after a simple work-up procedure. These generic conditions are ideal for proof of transformation, and as the starting point for development and optimization of a specific process. The discovery and fine-tuning of this generic protocol will be presented, supported extensively by examples to illustrate its scope and utility.

A facile synthesis of dibenzopyrroloazepinones as tetracyclic allocolchicinoids - An unusual 1,2-phenyl shift

A facile synthesis of dibenzopyrroloazepinones via an electrophilic cyclisation of a biphenyl-acyliminium ion is described; an unusual 1,2-phenyl shift occurs when the C-1′ carbon is the more nucleophilic than the C-2′ carbon.

The synthesis of substituted benzo[c]chromen-6-ones by a Suzuki coupling and lactonization sequence using ionic liquids - From laboratory scale to multi-kilogram synthesis

A series of benzo[c]chromen-6-ones are prepared by a Suzuki coupling and lactonization sequence starting with 2-methoxyphenylboronic acids and methyl 2-bromobenzoate derivatives. The use of ionic liquids in this synthesis has been explored. It was found that the Suzuki coupling proceeds much faster when a catalytic amount of the ionic liquid [BMIM][PF6] is used. By using the Lewis acidic ionic liquids [BMIM][Al2Cl7] or [TMAH][Al2Cl7] the methyl 2-(2-methoxyphenyl)benzoate product obtained from the Suzuki coupling can be converted to benzo[c]chromen-6-ones in one step, while the conventional route involves three steps. The use of ionic liquids is demonstrated in the synthesis of a variety of benzo[c]chromen-6-ones. It is also shown that the application of ionic liquids is not limited to laboratory scale experiments, as a process was developed and performed on a multi-kilogram scale. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

A water-compatible, highly active and reusable PEG-coated mesoporous silica-supported palladium complex and its application in Suzuki coupling reactions

A highly active heterogeneous palladium catalyst was prepared from coated mesoporous materials which contain a layer of readily available PEG with a labile coordinating ability for palladium. The aqueous suspension of the catalyst may be reused several times by simple extraction of the aqueous reaction mixture with ether to remove the product. The Royal Society of Chemistry 2006.

Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure

Suzuki-Miyaura coupling reactions of aryl and heteroaryl halides with aryl-, heteroaryl- and vinylboronic acids proceed in very good to excellent yield with the use of 2-(2′,6′-dimethoxybiphenyl) dicyclohexylphosphine, SPhos (1). This ligand confers unprecedented activity for these processes, allowing reactions to be performed at low catalyst levels, to prepare extremely hindered biaryls and to be carried out, in general, for reactions of aryl chlorides at room temperature. Additionally, structural studies of various 1·Pd complexes are presented along with computational data that help elucidate the efficacy that 1 imparts on Suzuki-Miyaura coupling processes. Moreover, a comparison of the reactions with 1 and with 2-(2′,4′,6′-triisopropylbiphenyl)diphenylphosphine (2) is presented that is informative in determining the relative importance of ligand bulk and electron-donating ability in the high activity of catalysts derived from ligands of this type. Further, when the aryl bromide becomes too hindered, an interesting C-H bond functionalization-cross-coupling sequence intervenes to provide product in high yield.

Suzuki-Miyaura coupling with high turnover number using an N-acyl-N-heterocyclic carbene palladacycle precursor

A simple N-acylimidazolium salt precursor to a NHC-complexed palladacyclic ligand gives high turnover numbers (107) for Suzuki-Miyaura coupling and is applied to the preparation of biaryls used in the synthesis of coumarins. The results suggest that N-acyl-NHC derivatives can contribute to further expanding the rich chemistry of NHCs.

Synthesis of unsymmetrical biaryls by electroreductive cobalt-catalyzed cross-coupling of aryl halides

The consumable anode process allows the electrochemical cross-coupling reaction between various functionalized aromatic halides (iodides, bromides and chlorides) in the presence of cobalt halides as catalyst in a mixed solvent acetonitrile/pyridine (9:1). A great variety of unsymmetrical biaryls are obtained in moderate to excellent yields.