71426-20-5

Upstream product

• 28715-70-0 methoxy-phenyl-sulfane 
• 2746-25-0 p-Methoxybenzyl bromide 
• 31268-20-9 bromomethyl phenyl sulfoxide 
• 5720-07-0 4-methoxyphenylboronic acid 
• 108-98-5 thiophenol 
• 824-94-2 p-methoxybenzyl chloride 
• 6258-60-2 p-methoxybenzylmercaptan 
• 5023-67-6 4-methoxybenzyl phenyl sulfide 
• 623-12-1 4-chloromethoxybenzene 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 623-00-7 4-bromobenzenecarbonitrile 
• 6952-59-6 3-cyanobromobenzene 
• 104-93-8 p-methylanizole 

Downstream Products

• 214207-25-7 1-(4-methoxyphenyl)-4-phenyl-1-phenylsulfinyl-2-butanol 
• 17259-54-0 1-(4-methoxybenzyl)pyridin-2(1H)-one 
• 303144-04-9 1-acetoxy-1-[(1-methoxyphenyl)(phenylsulfinyl)methyl]cyclohexane 
• 303143-93-3 2-mesyloxy-1-(4-methoxyphenyl)-4-phenyl-1-phenylsulfinylbutane 
• 7577-08-4 1-(cyclohexylidenemethyl)-4-methoxy-benzene 
• 22920-31-6 (E)-1-(4-methoxyphenyl)-2-(1-naphthyl)ethene 
• 56041-27-1 (E)-1-(4-methoxyphenyl)-2-(3,4-methylenedioxyphenyl)ethene 
• 150660-28-9 (E)-1-methoxy-4-(4-phenylbut-1-en-1-yl)benzene 
• 303144-01-6 1-[(1-methoxyphenyl)(phenylsulfinyl)methyl]cyclohexanol 
• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 35103-34-5 N-(p-methoxybenzyl)acetamide 
• 105-13-5 4-Methoxybenzyl alcohol 
• 104-21-2 p-methoxybenzyl acetate 
• 55539-39-4 p-methoxybenzylphenylsulfone 

Relevant academic research and scientific papers

Synthesis of: N -alkylated 2-pyridones through Pummerer type reactions of activated sulfoxides and 2-fluoropyridine derivatives

N-Alkylated 2-pyridone products were obtained in good to excellent yields through a one-pot procedure involving either normal or interrupted Pummerer reactions between triflic anhydride activated sulfoxides and 2-fluoropyridine derivatives, followed by hydrolysis. This is a rare case that uses 2-fluoropyridine as a nucleophile in Pummerer type reactions.

Palladium/PC-Phos-Catalyzed Enantioselective Arylation of General Sulfenate Anions: Scope and Synthetic Applications

Herein we reported an efficient palladium-catalyzed enantioselective arylation of both alkyl and aryl sulfenate anions to deliver various chiral sulfoxides in good yields (up to 98%) with excellent enantioselectivities (up to 99% ee) by the use of our developed chiral O,P-ligands (PC-Phos). PC-Phos are easily prepared in short steps from inexpensive commercially available starting materials. The single-crystal structure of the PC4/PdCl2 showed that a rarely observed 11-membered ring was formed via the O,P-coordination with the palladium(II) center. The salient features of this method include general substrate scope, ease of scale-up, applicable to the late-stage modification of bioactive compounds, and the synthesis of a marketed medicine Sulindac.

Tetrabutylammonium tribromide impregnated MCM-48 as a heterogeneous catalyst for selective oxidation of sulfides

We report here tetrabutylammonium tribromide supported on MCM-48 as a highly efficient heterogeneous catalyst for the selective oxidation of sulfides, in ethanolic medium using hydrogen peroxide as an oxidant. The aforementioned oxidation reactions were found to proceed rapidly (20 min) and in good yield (85-99%) (17 examples). The oxidation products were characterized by 1H NMR, 13C NMR and elemental analysis. The catalytic properties were analysed by TEM, XRD and BET-surface area measurement. No over-oxidation of the substrates was observed (analysed by GC), and the catalyst was effectively recycled for five consecutive cycles without any significant loss in its catalytic activity.

Palladium-catalyzed direct arylation of methyl sulfoxides with aryl halides

The palladium-catalyzed α-arylation of unactivated sulfoxides has been developed. The weakly acidic α-protons of sulfoxides are reversibly deprotonated by LiOtBu, and a palladium phosphine complex facilitates the arylation. A variety of aryl methyl sulfoxides were coupled with aryl bromides. More challenging coupling partners, such as alkyl methyl sulfoxides (including dimethyl sulfoxide) and aryl chlorides proved to be suitable under the optimized conditions. This method was utilized to synthesize bioactive benzyl sulfoxide intermediates.

Competitive and selective Csp3-Br versus Csp2-Br bond activation in palladium-catalysed Suzuki cross-coupling: An experimental and theoretical study of the role of phosphine ligands

Phosphine ligands have been demonstrated to have an effect on reactivity and selectivity in the competitive intramolecular palladium-catalysed Suzuki-Miyaura coupling of dibromo sulfoxide 1a possessing two different hybridised electrophilic carbons. It was found that the bromine bond to the sp3-hybridised carbon is selectively replaced in the presence of unhindered phosphines such as PPh3 or xantphos. The use of hindered phosphine ligands such as P(o-tol)3 and P(1-naphthyl)3 reversed the selectivity, conducting the cross-coupling at the Csp 2-Br. Identical trends were observed in external competition experiments carried out with bromomethyl sulfoxide and different substituted bromoarenes. DFT and DFT/MM calculations showed that the selectivity observed is mainly due to the different facility of the ligands to dissociate. Bisphosphine catalysts favour coupling at the sp3 carbon, whereas monophosphine catalysts prefer the sp2 carbon. Customised catalysts: Proper selection of the phosphine ligand in the palladium catalyst enables a highly intra- and intermolecular selective Suzuki-Miyaura coupling at either Csp 3-Br or Csp2-Br (see figure). DFT and DFT/MM calculations show that the selectivity observed is mainly due to the different facilities of the ligands for dissociation. Copyright

Palladium-catalyzed reaction of boronic acids with chiral and racemic α-bromo sulfoxides

Palladium-catalyzed cross-coupling reactions of racemic α-bromo sulfoxides with boronic acids are carried out in either aqueous or nonaqueous medium with formation of a new C sp3-C sp2 bond. The arylation of chiral α-bromo sulfoxides occurs without racemization. The cross-coupling reaction is general and gives high yields with arylboronic acids substituted with either donor or acceptor groups but gives poor results with heteroarylboronic acids. The best yields are obtained using degassed solvents and CsF instead of aqueous base. The use of aqueous base and the presence of oxygen favor the homocoupling side reaction.

The oxidation of sulfides by chromium(V)

The mechanism for the oxidation of sulfides by [(me4-salen)CrV(O)(pyO)]CF3SO3, where me4-salen is 8,8,8',8'-tetramethylsalen and pyO is pyridine N-oxide, has been investigated. Results from Hammett correlations on the rates of oxidation of substituted thioanisoles, frontier molecular orbital calculations, and product studies are consistent with a mechanism that is initiated by a single electron transfer to give a radical cation intermediate.

Unprecedented palladium-catalyzed cross-coupling reaction of α-bromo sulfoxides with boronic acids

(Matrix presented) A new Suzuki-type palladium-catalyzed reaction of boronic acids with α-bromo sulfoxides has been developed using a protocol similar to the well-documented reaction of boronic acids with aryl halides. Both cross-coupling and homocoupling processes were observed. The best yields in cross-coupling products were obtained when the presence of oxygen was carefully excluded using degassed solvents. The oxidative addition palladium complex intermediate could be isolated and characterized by X-ray single-crystal diffraction.

Lewis acid assisted permanganate oxidations

Lewis acids combine with permanganate in acetone solutions to form a complex that has enhanced oxidizing capabilities. The use of Lewis acids under these conditions to promote permanganate oxidations is superior to the use of Bronsted acids because the latter promote enolization of the solvent and subsequent unproductive reduction of the oxidant. The products obtained from a variety of alkenes, alkynes, arenes, sulfides, alcohols and ethers have been identified and probable reaction mechanisms proposed.

The Mechanism of Enzymatic and Biomimetic Oxidations of Aromatic Sulfides and Sulfoxides

Biomimetic and enzymatic oxidations of benzyl sulfides and sulfoxides lead to products (sulfoxides or sulfones) different from those obtained with bona fide electron transfer oxidations (products of C-H and/or C-S bond cleavage), which suggests the operation of an oxygen transfer machanism.