89951-79-1

Usage

Synthesis

To a suspension of potassium flfluoride (350 mg, 6.0 mmol, spray dried) in DMF (50 mL) were added ethyldiflfluoro-(4-methyl)silane (560 mg, 3.0 mmol), 3-iodobenzyl alcohol (250 mg, 2.0 mmol), and (η3 -C3H5PdCl)2 (37 mg, 0.1 mmol). The resulting mixture was stirred at 100 °C for 15 h, cooled to room temperature, poured into saturated aqueous sodium bicarbonate solution, and extracted with diethyl ether (3 × 20 mL). The combined ethereal layer was then dried over magnesium sulfate. The solvent was removed under reduced pressure. The crude material was purifified by silica gel chromatography eluting a mixture of hexane:EtOAc (5:1) to give 340 mg (86%) of 3-hydroxymethyl-4′-methylbiphenyl as a colorless solid.Reference: Hatanaka, Y; Goda, K.; Okahara, Y.; Hiyama, T. Tetrahedron 1994, 50, 8301?8316.

Upstream product

• 5720-05-8 4-methylphenylboronic acid 
• 208941-39-3 4-(4-Carboxy-butoxy)-benzoic acid 3-iodo-benzyl ester 
• 624-31-7 4-tolyl iodide 
• 87199-15-3 [3-(hydroxymethyl)phenyl]boronic acid 
• 57455-06-8 3-iodobenzylalcohol 
• 5142-75-6 tri(p-tolyl)bismuth 
• 873-63-2 m-chlorobenzyl alcohol 
• 106-38-7 para-bromotoluene 
• 135273-60-8 (dichloro)(ethyl)(4-methylphenyl)silane 
• 35005-21-1 4-(4-Carboxy-butoxy)-benzoic acid 
• 126485-51-6 ethyl(difluoro)(4-methylphenyl)silane 

Relevant academic research and scientific papers

Pd-catalyzed atom-efficient cross-coupling of triarylbismuth reagents with protecting group-free iodophenylmethanols: Synthesis of biarylmethanols

An atom-efficient procedure for the synthesis of functionalized biarylmethanols via the Pd-catalyzed cross-coupling reactions of differently functionalized iodophenylmethanols and triarylbismuth reagents is described. This protecting group-free direct couplings of 2-, 3- or 4-iodophenylmethanols with triarylbismuth reagents afforded biarylmethanols in good to high yields.

Development of unimolecular tetrakis(piperidin-4-ol) as a ligand for Suzuki-Miyaura cross-coupling reactions: Synthesis of incrustoporin and preclamol

Abstract A domino aza-Cope/aza-Prins cascade enabled the synthesis of a new class of 4-hydroxypiperidine-appended mono, bis, tris, and tetrakis unimolecular compounds that served as efficient ligands to catalyze Suzuki-Miyaura cross-coupling reactions under aerobic conditions. Various biaryls, terphenyls, and heterocyclic biphenyls were obtained in good to excellent yields. The ligands were also capable of catalyzing the Heck-Mizoroki reaction. As an application, the Suzuki-Miyaura coupling reaction was used in the synthesis of incrustoporin, its analogs, and the drug molecule preclamol. A domino aza-Cope/aza-Prins cascade enabled the synthesis of a new class of 4-hydroxypiperidine-appended mono-, bis-, tris-, and tetrakis-unimolecular compounds that served as efficient ligands to catalyze Suzuki-Miyaura cross-coupling reactions under aerobic conditions. Various biaryls, terphenyls, and heterocyclic biphenyls were obtained in good to excellent yields.

A General Suzuki-Miyaura Coupling of Aryl Chlorides with Potassium Aryltrifluoroborates in Water Catalyzed by an Efficient CPCy Phendole-phos-Palladium Complex

General examples of the palladium-catalyzed Suzuki-Miyaura cross-coupling of aryl or heteroaryl chlorides with potassium aryl- or heteroaryltrifluoroborates in water are presented. The palladium complex comprising of palladium(II) acetate and 'CPCy Phendole-phos' is found to be a highly effective catalyst system for this coupling reaction with low catalyst loading (down to 0.005 mol% Pd).

Studies on Pd/NiFe2O4 catalyzed ligand-free Suzuki reaction in aqueous phase: Synthesis of biaryls, terphenyls and polyaryls

Palladium supported on nickel ferrite (Pd/NiF2O4) was found to be a highly active catalyst for the Suzuki coupling reaction between various aryl halides and arylboronic acids. The reaction gave excellent yields (70-98%) under ligand free conditions in a 1:1 DMF/H2O solvent mixture, in short reaction times (10-60 min). The catalyst could be recovered easily by applying an external magnetic field. The polyaryls were similarly synthesized.

Studies on phosphine free Pd-salen complexes as effective catalysts for aqueous Suzuki reaction

Palladium complexes of the salen ligands, N,N'-bis(salicylidene)- ethylenediamine and N,N'-bis(salicylidene)-1,.-phenylenediamine have been explored for their catalytic activity in a phosphine-free aqueous Suzuki reaction. The various reaction parameters have been systematically optimized with respect to various solvents, bases, temperatures and Pd concentrations. The studies conclude that 1:1 DMF to water solvent ratio, Na2CO 3 as base and 0.5 mo1% of palladium at 90°C is apt for Suzuki reactions. Rapid transformation of substituted aryl iodides and aryl bromides into corresponding biaryls has been observed with excellent yield ranging from 70-86%, under optimized conditions.

Pd-mediated C-C and C-S bond formation on solid support: A scope and limitations study

The scope and limitations of Pd(0)-mediated coupling reactions between aromatic halides linked to a polystyrene resin and boronic acid derivatives (Suzuki coupling), aromatic and vinylic tin compounds (Stille coupling), as well as thiols are reported. For all reactions, conditions were optimized and evaluated with various reagents. In many cases, upon cleavage from the solid support, products were obtained in excellent yields. In most cases, the optimized reaction conditions are superior to those previously reported in the literature.

Highly Selective Cross-Coupling Reactions of Aryl(halo)silanes with Aryl Halides: A General and Practical Route to Functionalized Biaryls

The palladium catalyzed cross-coupling reaction of aryl halides with aryl(halo)silanes (halogen=F, Cl) gives good yields of unsymmetrical biaryls and p-terphenyls.The reaction takes place smoothly in N,N-dimethylformamide in the presence of an appropriate palladium catalyst and potassium fluoride.Since this reaction is tolerant of a variety of reactive functional groups, highly functionalized 4,4'-, 3,4'-, 2,4'- and even sterically crowded 2,2'-disubstituted biaryls can be obtained in moderate to high yields.The synthetic utility of the method has been demonstrated by its application to a short synthesis of liquid crystals.Mechanistic aspects of transmetalation of an aryl(fluoro)silicate intermediate with a palladium complex are discussed on the basis of the substituent effects on the rate of the cross-coupling reactions.

Selective Synthesis of Unsymmetrical Biaryls via Palladium-Catalyzed Cross-Coupling of Arylfluorosilanes with Aryl Iodides

In the presence of potassium fluoride, arylfluorosilanes readily participate in Pd-catalyzed cross-coupling reaction of aryl iodides to give the corresponding unsymmetrical biaryls in good yields.