Cross-coupling Reaction Of Arylboronic Acids Research Articles

ChemInform Abstract: Synthesis of Sterically Hindered Biaryls (III), (V), and (VII) via the Palladium-Catalyzed Cross-Coupling Reaction of Arylboronic Acids or Their Esters with Haloarenes.

ChemInform Abstract: Synthesis of Sterically Hindered Biaryls (III), (V), and (VII) via the Palladium-Catalyzed Cross-Coupling Reaction of Arylboronic Acids or Their Esters with Haloarenes.

ChemInform Abstract: A Simple Asymmetric Synthesis of 4-Arylphenylalanines via Palladium- Catalyzed Cross-Coupling Reaction of Arylboronic Acids with Tyrosine Triflate.

ChemInform Abstract: A Simple Asymmetric Synthesis of 4-Arylphenylalanines via Palladium- Catalyzed Cross-Coupling Reaction of Arylboronic Acids with Tyrosine Triflate.

ChemInform Abstract: Synthesis of Unsymmetrical Biaryl Ketones (IV) via Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids (I) with Iodoarenes (II).

ChemInform Abstract: Synthesis of Unsymmetrical Biaryl Ketones (IV) via Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids (I) with Iodoarenes (II).

CuO-2,2′-Diamino-6,6′-Dimethylbiphenyl Catalyzed Suzuki–Miyaura Coupling Reactions of Arylboronic Acids with Aryl Iodides and Bromides

CuO-catalyzed Suzuki–Miyaura cross-coupling reactions of arylboronic acids with aryl iodides and bromides using 2,2′-diamino-6,6′-dimethylbiphenyl as the ligand are described in the paper. Under suitable conditions, all reactions gave the desired coupling products in moderate to excellent yields.

ChemInform Abstract: Synthesis of Biaryls via Nickel-Catalyzed Cross-Coupling Reaction of Arylboronic Acids and Aryl Mesylates.

Abstract The cross-coupling reaction of arylboronic acids (1.3 equivs) with aryl methane-sulfonates was carried out in the presence of a nickel(0) catalyst (3 mol%) and K 3 PO 4 ·nH 2 O (3 equivs). The use of toluene as the solvent and the nickel(0)-dppf catalyst prepared from NiCl 2 (dppf) plus dppf with BuLi were recognized to be the most efficient to achieve both high yields and high selectivity. The reaction can be applied to various electron-deficient and -rich aryl methanesulfonates to give high yields.

Synthesis of Functionalized Isoquinolines via Sequential Cyclization/Cross-Coupling Reactions

CuX(2)-mediated cyclization of 2-alkynylbenzaldehyde O-methyl oximes in N,N-dimethylacetamide (DMA) gave rise to 4-chloroisoquinolines in good yield, which underwent the palladium-catalyzed cross-coupling reactions of arylboronic acids subsequently to afford the functionalized isoquinolines.

Heterogeneous catalyzed aryl–nitrogen bond formations using a valine derivative bridged metal–organic coordination polymer

A new 1D macrocyclic copper(ii) coordination polymer, [Cu(2)] (, = N-(4-pyridyl)-d,l-valine), based on a valine derived ligand was synthesized and characterized by single-crystal X-ray diffraction studies. The catalytic experiments showed that compound was an efficient catalyst for the cross-coupling reaction of arylboronic acids with imidazole in the absence of additional additives. The crystal structure analysis of suggested that the vacant axial coordination position of the copper(ii) atoms played a very important role in the efficient catalytic transformation process.

Lewis acid InBr3-catalyzed arylation of diorgano diselenides and ditellurides with arylboronic acids

A novel Lewis acid InBr3-catalyzed direct cross-coupling reaction of arylboronic acids with diorgano diselenides and ditellurides without any additive has been developed. The reactions generated the corresponding unsymmetrical diorgano monoselenides and monotellurides in good to excellent yields. The method has advantages of broad substrate scope, simple operation, mild reaction conditions and high effectiveness. A possible reaction mechanism was proposed.

Synthesis of Aryl Ketones by Cross-Coupling Reaction of Arylboronic Acids with Carboxylic Anhydrides in Aqueous Phase

A highly efficient aqueous system of PdCl2-catalyzed cross-coupling reaction of arylboronic acid with carboxylic anhydride (Suzuki-type reaction) without the use of phosphine ligands was developed. The reactions went smoothly in acetone/H2O phase to give good yields of aryl ketones in short reaction times (1–3 h) at room temperature in air and were unaffected by the presence of electron-releasing and electron-withdrawing substituents in both the arylboronic acids and carboxylic anhydrides.

Efficient Synthesis of Symmetrically and Unsymmetrically Substituted Hexaphenylbenzene Analogues by Suzuki–Miyaura Coupling Reactions

A series of symmetrically and unsymmetrically substituted hexaphenylbenzene (HPB) analogues were efficiently synthesized by using a sterically hindered Suzuki-Miyaura cross-coupling reaction of arylboronic acids with 1,4-diiodo-2,3,5,6-tetraarylbenzenes under our optimized reaction conditions. The 1,4-diiodo-2,3,5,6-tetraarylbenzenes can be readily prepared by using a one-pot Hart reaction. Oxidative cyclodehydrogenation of the dibromo derivative with FeCl(3) gave the corresponding hexabenzocoronene (HBC) derivative in good yield.

Pd-catalyzed Suzuki–Miyaura reactions of aryl halides using bulky biarylmonophosphine ligands

The following protocol describes the application of a highly active Pd-based catalyst system in the Suzuki-Miyaura cross-coupling reaction of arylboronic acids with aryl chlorides to provide biaryl compounds. The general procedure includes a detailed description of an appropriate reaction setup, two methods for assaying the crude reaction mixture (GC and TLC) and a procedure for the isolation, purification and characterization of the anticipated product. Reagents and catalyst precursors can be manipulated in the air; however, the cross-coupling reactions must be performed in an inert atmosphere. Two Suzuki-Miyaura reactions are included in the text as representative examples of these procedures. Although the reactions can proceed in less than 5 min, the protocols, including workup, generally take 6-30 h to be completed.

Pd-Catalyzed Synthesis of C4-Aryl Pyrimidinone Nucleoside Analogues

A two-step synthesis of C4-aryl pyri­midinone nucleoside analogues from readily available thymidine is described, which involves O4-arylsulfonylation and then Suzuki cross-coupling reaction of arylboronic acids with the derived O4-mesylates. Most of the coupling reactions proceed efficiently at room temperature in toluene, and electron-deficient arylboronic acids may also be cross-coupled at elevated temperature in THP.

Phosphine ligand and base-free, Pd- catalyzed oxidative cross-coupling reaction of arylboronic acids with arylmercuric acetates

Arylmercuric acetates have been found to undergo Suzuki type cross coupling reactions with arylboronic acids catalyzed by palladium salts in non-polar solvents under ambient conditions to give biaryl derivatives in high yields. The reaction is mild and does not require any organic or inorganic base nor a phosphine ligand.

The Surfactant-Promoted Cross-Coupling Reactions of Arylboronic Acids with Carboxylic Anhydrides or Acyl Chlorides in Water

The palladium(II) chloride catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides in water in the presence of various surfactants is described. The inexpensive and industrially widely used sodium dodecyl sulfate (SDS) was found to be a good promoter of the coupling reaction and aryl ketones were obtained in good yields without the use of phosphine ligands. The reactions were unaffected by the presence of electron-releasing and electron-withdrawing substituents in both the arylboronic acids and carboxylic derivatives and a variety of aryl ketones were obtained under mild conditions in air.

Microwave‐Assisted Suzuki Reactions for the Preparation of the Antifungal 3‐Aryl‐5‐methyl‐2,5‐dihydrofuran‐2‐ones.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Microwave Assisted Suzuki Reactions for the Preparation of the Antifungal 3-Aryl-5-methyl-2,5-dihydrofuran-2-ones

The Suzuki cross-coupling reaction of arylboronic acids with a bromo-furanone has been developed to prepare a series of substituted 2,5-dihydrofuran-2-ones related to the fungal metabolite, incrustoporin. A protocol of microwave heating was introduced to improve synthesis throughput.

Pyrrolodiazines. 6. Palladium-Catalyzed Arylation, Heteroarylation, and Amination of 3,4-Dihydropyrrolo[1,2-a]pyrazines

The palladium-catalyzed Suzuki cross-coupling reaction of arylboronic acids and 6-bromo- and 6,8-dibromo-3,4-dihydropyrrolo[1,2-a]pyrazines afforded 6-substituted and 6,8-disubstituted 3,4-dihydropyrrolo[1,2-a]pyrazines in good yields. Stille and Negishi coupling reactions have been used to prepare 6-heteroaryl-substituted derivatives in moderate yields by employing heteroaryl halides and 6-metalated 3,4-dihydropyrrolo[1,2-a]pyrazines as reaction partners. A variety of cyclic secondary amines have also been incorporated at position C-6 of 6-bromo-1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazine in the presence of the palladium catalyst Pd(2)(dba)(3) in conjunction with BINAP as ligand. This amination reaction is one of the few reported examples of such a palladium-catalyzed transformation on a pyrrole ring, although the reaction could not be extended to less nucleophilic amines.

A Convenient Method for Preparing Aromatic α,β‐Unsaturated Ketones from α,β‐Unsaturated Acyl Chlorides and Arylboronic Acids via Suzuki—Miyaura Type Coupling Reaction.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Palladium Catalyzed Suzuki Cross‐coupling Reaction in Molten Tetra‐r)‐butylammonium Bromide

AbstractA practical procedure for palladium catalyzed Suzuki cross‐coupling reaction of arylboronic acids with aryl halides, including aryl chlorides in molten tetra‐n‐butylammonium bromide (TBAB) was developed. The reaction exhibits high efficiency and functional group tolerance. The recovery of the catalyst and molten n‐Bu4NBr was also investigated.

Synthesis, mesomorphic behaviour and optical anisotropy of some novel materials for nematic mixtures of high birefringenceElectronic supplementary information (ESI) available: experimental procedures for all compounds not already given in this paper. See http://www.rsc.org/suppdata/jm/b4/b400630e/

Structural moieties including core units (such as phenyl, naphthyl and thiophenyl), linking groups (such as ethynyl), terminal substituents (such as cyano, isothiocyanato and fluoro), and lateral fluoro substituents have been incorporated into novel materials designed to confer a high birefringence on nematic mixtures. The materials have all been prepared through convergent syntheses involving palladium-catalysed cross-coupling reactions of arylboronic acids. The materials were examined for their mesomorphic behaviour as neat materials and as mixtures; some materials were found to have extremely high nematic phase stability, and others were non-mesogenic. The materials were evaluated in nematic host mixtures for their optical anisotropy, and they were all found to show promisingly high values.