Cross-coupling Reaction Of Arylboronic Acids Research Articles

Simple and Efficient Protocol for the Synthesis of Functionalized Styrenes from 1,2‐Dibromoethane and Arylboronic Acids.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Simple and efficient protocol for the synthesis of functionalized styrenes from 1,2-dibromoethane and arylboronic acids.

[reaction: see text] A simple and efficient protocol for the preparation of functionalized styrenes is disclosed that employs the palladium-catalyzed cross-coupling reaction of arylboronic acids with vinyl bromide, generated in situ from 1,2-dibromoethane. The reaction is carried out under mild reaction conditions. Compared with the cross-coupling reactions usually employed to obtain vinylarenes, this protocol is very simple, overcomes the inconvenience of using of ethylene under pressure, and uses air-stable and widely available arylboronic acids instead of vinyl organometallic reagents.

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

Aromatic α,β-unsaturatetl ketones are synthesized efficiently by palladium-catalyzed cross-coupling reaction of arylboronic acids with α,β-unsaturated acyl chlorides in the presence of K 3 PO 4 hydrate in toluene.

Palladium-catalyzed cross-coupling reactions of arylboronic acids and 2-I- p-carborane

p-Carborane has been arylated on the 2- B-atom in high yields, using the Suzuki–Miyaura reaction. Thus the reaction between 2-I- p-carborane and various arylboronic acids [1-naphthyl-, phenyl-, 4-MeOC 6H 4, 3-CH 3CONHC 6H 4, 4-NCC 6H 4, 3-NO 2C 6H 4], gave the corresponding 2-aryl- p-carboranes in DME solution when reacted in the presence of cesium fluoride and the catalytic Pd 2(dba) 3–dppb system.

Remarkable co-catalysis by copper(I) oxide in the palladium catalyzed cross-coupling of arylboronic acids with ethyl bromoacetate.

Copper(I) oxide can effectively co-catalyze the Suzuki type cross-coupling reactions of arylboronic acids with ethyl bromoacetate. As an alternative protocol for introducing the methylenecarboxy group into functionalized molecules, this reaction occurs in the absence of highly toxic thallium compounds or special ligands and should be convenient and practical.

N-arylation of primary and secondary aliphatic amines on solid supports.

A general and mild method for the N-arylation of primary and secondary aliphatic amines is reported. Copper acetate, triethylamine mediated C/N cross-coupling reaction of arylboronic acids at room temperature to solid-supported primary and secondary amines gave good to excellent yields of the desired N-arylated products.

Facile stereoselective syntheses of aryl substituted α,β‐unsaturated esters containing a trifluoromethyl group

AbstractThe Suzuki‐type cross‐coupling reaction of arylboronic acids 3 with ethyl (Z)‐3‐iodo‐4,4,4‐trifluoro‐2‐butenoate 2, which was generated by hydroiodination of available ethyl 4,4,4‐trifluoro‐2‐butynoate 1, to afford ethyl (E)‐3‐aryl‐4,4,4‐trifluoro‐2‐butenoates 4, was studied for the first time. It was found that under the optimum conditions the cross‐coupling reaction could readily give 4 as the sole E‐isomer in 76–91% yields. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:287–290, 2002; Published online in Wiley Interscience (www.interscience.wiley.com). DOI 10.1002/hc.10032

Preparation of 3-aryl-substituted salicylaldehydes via Suzuki coupling

An efficient method for the preparation of 3-arylsalicylaldehydes by palladium-catalyzed cross-coupling reaction of arylboronic acids and 3-bromo-5- tert-butylsalicylaldehyde is described. Parallel catalyst screening allowed rapid optimization of the reaction conditions.

Synthesis of Biaryls via Cross-Coupling Reaction of Arylboronic Acids with Aryl Chlorides Catalyzed by NiCl 2/Triphenylphosphine Complexes

The cross-coupling reaction of tolylboronic acids (1.3 equiv.) with chloroarenes in toluene was carried out at 80–100°C in the presence of a NiCl 2/PPh 3 catalyst (3 mol%) and K 3PO 4· nH 2O (2.6 equiv.). The reaction can be applied to various electron-deficient and -rich chloroarenes and is economical as the industrial process.

The Cross-Coupling Reaction of Arylboronic Acids with Chloropyridines and Electron-Deficient Chloroarenes Catalyzed by a Polymer-Bound Palladium Complex

The cross-coupling reaction of tolylboronic acids (1.3 equiv.) with chloropyridines, chloroquinoline, or activated chloroarenes having an electron-withdrawing group was carried out in toluene at 80°C in the presence of a polymer-bound PdCl 2 catalyst (3 mol%) and aqueous 2 M K 3PO 4 (2.6 equiv.). The palladium–phosphine complex supported on a polystyrene–PPh 2 resin was reused with no significant decrease in activity.

A convenient palladium/ligand catalyst for Suzuki cross-coupling reactions of arylboronic acids and aryl chlorides

The Pd/ligand A catalyst efficiently catalyzes general Suzuki biaryl cross-coupling reactions of arylboronic acids and aryl chlorides.

Synthesis of biaryls via nickel-catalyzed cross-coupling reaction of arylboronic acids and aryl mesylates

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 3PO 4·nH 2O (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.

Palladium-Catalyzed Carbonylative Cross-Coupling Reaction of Arylboronic Acids with Aryl Electrophiles: Synthesis of Biaryl Ketones

The carbonylative cross-coupling reaction of arylboronic acids with aryl electrophiles (ArI, ArBr, and ArOTf) to yield unsymmetrical biaryl ketones was carried out in anisole at 80 °C in the presence of a palladium catalyst and a base. The reaction selectively proceeded under an atmospheric pressure of carbon monoxide when PdCl2(PPh3)2 (3 mol %)/K2CO3 (3 equiv) were used for aryl iodides and PdCl2(dppf) (3 mol %)/K2CO3 (3 equiv)/KI (3 equiv) for the bromides or the triflates. The carbonylation of arylboronic acids with benzyl halides gave aryl benzyl ketones.

A Suzuki coupling approach to double bonds locked analogues of strobilurin A

Four double bonds locked analogues of strobilurin A were first synthesized via palladium(0)-catalyzed cross-coupling reaction of arylboronic acids with vinyl and aryl bromides.

Synthesis of unsymmetrical biaryl ketones via palladium-catalyzed carbonylative cross-coupling reaction of arylboronic acids with iodoarenes

The cross-coupling reaction between arylboronic acids, carbon monoxide (1 atm), and aryl iodides in the presence of palladium catalyst and base provided unsymmetrical biaryl ketones in high yields. The choice of a suitable base and solvent was essential to achieve selective formation of the unsymmetrical biaryl ketone without a biaryl by-product.

Palladium-catalysed cross-coupling reactions of arylboronic acids with π-deficient heteroaryl chlorides

The palladium-catalysed cross-coupling reactions of arylboronic acids with a variety of π-deficient heteroaryl chlorides proceed in high yield. [1,4-Bis(diphenylphosphino)butane]palladium(II) dichloride was found to be a very satisfactory catalyst for monocyclic heteroaryl chlorides, whereas tetrakis(triphenylphosphine)palladium(O) was found to be excellent for a range of chloroquinoline derivatives.

Synthesis of Sterically Hindered Biaryls via the Palladium-Catalyzed Cross-Coupling Reaction of Arylboronic Acids or their Esters with Haloarenes

Synthesis of Sterically Hindered Biaryls via the Palladium-Catalyzed Cross-Coupling Reaction of Arylboronic Acids or their Esters with Haloarenes