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Ethyl 4''-methoxybiphenyl-4-carboxylate

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 696-62-8 para-iodoanisole 
• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 22868-26-4 (p-methoxyphenyl)dimethylsilanol 
• 4334-88-7 p-ethoxycarbonylphenylboronic acid 
• 64-17-5 ethanol 
• 7335-27-5 ethyl 4-chlorobenzoate 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 1879-16-9 1-methoxy-4-methylsulfanyl-benzene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 496922-59-9 N-benzyl-N-(1-octynyl)-p-toluenesulfonamide 
• 571903-64-5 4-(ethoxycarbonyl)phenylmagnesium chloride 

Relevant academic research and scientific papers

Palladium-Catalyzed Three-Component Coupling of Ynamides

A palladium-catalyzed regioselective three-component coupling of ynamides was developed. The reaction proceeded smoothly to furnish the desired products when carried out at 70 °C in acetonitrile/water with potassium carbonate in the presence of 2.5 mol percent Pd2(dba)3·CHCl3 without a ligand. Various iodides and boronic acids were used in this reaction, and a carbon-carbon bond was formed with satisfactory regioselectivity from the ynamides.

Palladium-Catalyzed Cross-Coupling of Unactivated Aryl Sulfides with Arylzinc Reagents under Mild Conditions

Cross-coupling of general aryl alkyl sulfides with arylzinc reagents proceeds smoothly, even at room temperature or below, with a palladium-N-heterocyclic carbene (NHC) catalyst. When combined with reactions that are unique to organosulfurs, that is, the SNAr sulfanylation or Pummerer reaction, the cross-coupling offers interesting transformations that are otherwise difficult to achieve. An alkylsulfanyl group is preferentially converted whilst leaving the tosyloxy and chloro intact, which expands the variety of orthogonal cross-coupling.

Nickel-catalyzed cross-coupling of non-activated or functionalized aryl halides with aryl grignard reagents

Figure Presented New nickel complexes can efficiently catalyze cross-coupling of unactivated and deactivated aryl chlorides and fluorides with aryl Grignard reagents. The reaction can tolerate functional groups in aryl chlorides with or without the aid of additives, depending on the substrates (see scheme).

Efficient cobalt-catalyzed formation of unsymmetrical biaryl compounds and its application in the synthesis of a sartan intermediate

(Chemical Equation Presented) No prior preparation of the organometallic reagent is required in a cobalt-catalyzed coupling of two different aryl halides under mild conditions (see scheme). A broad spectrum of valuable biaryl compounds can be prepared in this way. Not only may a variety of reactive substituents be present, but heteroaryl halides and aryl triflates are also suitable substrates. DMF = N,N-dimethylformamide, FG = functional group.

Use of functionalized onium salts as a soluble support for organic synthesis

The invention relates to the use of a onium salt functionalized by at least one organic function, as a soluble support, in the presence of at least one organic solvent, for organic synthesis of a molecule, in a homogenous phase, by at least one transformation of said organic function. The onium salt enables the synthesized molecule to be released. The onium salt is present in liquid or solid form at room temperature and corresponds to formula A1+, X1?, wherein A1+ represents a cation and X1? represents an anion.

Palladium-catalyzed cross-coupling reactions of substituted aryl(dimethyl)silanols

Cesium carbonate and cesium hydroxide monohydrate are effective activators for the palladium-catalyzed cross-coupling of aryl(dimethyl)silanols with substituted aryl halides. Extensive optimization studies led to the identification of key variables (solvent, catalyst, additive, and hydration level) that influence the rate and selectivity of the process. Manipulation of these factors provides an effective coupling method of wide scope and generality. Electron-rich aryl(dimethyl)silanols undergo cross-coupling with aryl iodides and aryl bromides in high yields and high selectivity for the desired cross-coupling products. Alternatively, high yields of cross-coupling products could be obtained with electron-poor or ortho-substituted aryl(dimethyl)silanols when activated with cesium hydroxide monohydrate.

Polymer-Assisted Solution-Phase (PASP) Suzuki Couplings Employing an Anthracene-Tagged Palladium Catalyst

A general method for polymer-assisted solution-phase (PASP) Suzuki reactions employing a combination of anthracene-tagged palladium catalyst and anthracene-tagged boronic acid with a polymer-supported carbonate base is reported. The anthracene-tagged catalyst allows for the easy removal of the Pd catalyst along with the dissociated phosphine ligand and phosphine oxide byproducts by sequestration through a chemoselective Diels-Alder reaction with a maleimide resin. The polymer-supported carbonate base facilitates the removal of excess boronic acid and the borane-containing byproducts present at the end of the coupling reaction. The Suzuki coupling reaction can be efficiently conducted by using combinations of the anthracene-tagged Pd catalyst, polymer-supported carbonate base, and anthracene-tagged boronic acid to yield the desired product in high purity and yield without the use of chromatography.

Cross-coupling reactions of arylsilanols with substituted aryl halides

(Matrix presented) The palladium-catalyzed cross-coupling of arylsilanols with aryl iodides and aryl bromides (in the presence of cesium carbonate) furnished various biaryl products in high yield. An extensive series of optimizations led to the identifica

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.