1774-36-3

Usage

Synthesis Reference(s)

Synthetic Communications, 16, p. 1207, 1986 DOI: 10.1080/00397918608056367Tetrahedron Letters, 31, p. 4533, 1990 DOI: 10.1016/S0040-4039(00)97667-6

InChI:InChI=1/C14H14O3S/c1-16-11-3-7-13(8-4-11)18(15)14-9-5-12(17-2)6-10-14/h3-10H,1-2H3

Upstream product

• 3393-77-9 bis(4-methoxyphenyl)sulfide 
• 100-66-3 methoxybenzene 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 951-92-8 1-methoxyl-4-(phenylsulfinyl)benzene 
• 118268-73-8 p-methoxybenzenesulfinic acid allyl ester 
• 7446-70-0 aluminium trichloride 
• 7791-25-5 sulfuryl dichloride 
• 1013-23-6 Dibenzothiophene sulfoxide 
• 499140-11-3 benzyl (2S,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxylate 
• 499140-12-4 benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate 
• 7719-09-7 thionyl chloride 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 696-63-9 4-Methoxybenzenethiol 
• 31401-17-9 methyl p-methoxybenzenesulphinate 

Downstream Products

• 3112-80-9 bis(p-anisyl)sulfone 
• 1774-34-1 bis(4-hydroxyphenyl) sulfoxide 
• 3393-77-9 bis(4-methoxyphenyl)sulfide 
• 91815-50-8 tris-(4-methoxyphenyl)sulfonium methane sulfonate 
• 138723-23-6 isopropyl (4-methoxyphenyl) sulfoxide 
• 7205-71-2 (+)-(R)-isopropyl (4-methoxyphenyl) sulfoxide 
• 7205-71-2 (-)-(S)-isopropyl (4-methoxyphenyl) sulfoxide 
• 171364-79-7 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 197635-86-2 1-methyl-4-(octyn-1-yl)benzene 
• 39253-43-5 N-(4-methylphenyl)-4-methoxyaniline 
• 55440-60-3 iminobis(4-methoxyphenyl)-λ⁶-sulfanone 
• 213596-33-9 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Palladium-Catalyzed Sulfinylation of Aryl- And Alkenylborons with Sulfinate Esters

An efficient, direct sulfinylation of organoborons catalyzed by palladium is disclosed. Treatment of organoborons and sulfinate esters in the presence of a palladium precatalyst provided a broad range of sulfoxides. Various organosulfur compounds having oxidizable functional groups were successfully prepared through the sulfoxide synthesis.

Ni-Catalyzed Borylation of Aryl Sulfoxides

A nickel/N-heterocyclic carbene (NHC) catalytic system has been developed for the borylation of aryl sulfoxides with B2(neop)2 (neop=neopentyl glycolato). A wide range of aryl sulfoxides with different electronic and steric properties were converted into the corresponding arylboronic esters in good yields. The regioselective borylation of unsymmetric diaryl sulfoxides was also feasible leading to borylation of the sterically less encumbered aryl substituent. Competition experiments demonstrated that an electron-deficient aryl moiety reacts preferentially. The origin of the selectivity in the Ni-catalyzed borylation of electronically biased unsymmetrical diaryl sulfoxide lies in the oxidative addition step of the catalytic cycle, as oxidative addition of methoxyphenyl 4-(trifluoromethyl)phenyl sulfoxide to the Ni(0) complex occurs selectively to give the structurally characterized complex trans-[Ni(ICy)2(4-CF3-C6H4){(SO)-4-MeO-C6H4}] 4. For complex 5, the isomer trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I was structurally characterized in which the phenyl sulfinyl ligand is bound via the oxygen atom to nickel. In solution, the complex trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I is in equilibrium with the S-bonded isomer trans-[Ni(ICy)2(C6H5)(SOC6H5)] 5, as shown by NMR spectroscopy. DFT calculations reveal that these isomers are separated by a mere 0.3 kJ/mol (M06/def2-TZVP-level of theory) and connected via a transition state trans-[Ni(ICy)2(C6H5)(η2-{SO}-C6H5)], which lies only 10.8 kcal/mol above 5.

Electrochemical oxygenation of sulfides with molecular oxygen or water: Switchable preparation of sulfoxides and sulfones

A practical and eco-friendly method for the controllable aerobic oxygenation of sulfides by electrochemical catalysis was developed. The switchable preparation of sulfoxides and sulfones was effectively controlled by reaction time, in which both molecular oxygen and water can be used as the oxygen source under catalyst and external oxidant-free conditions. The electrochemical protocol features a broad substrate scope and excellent site selectivity and is successfully applied to the modification of some sulfide-containing pharmaceuticals and their derivatives. This journal is

Electrochemical Thiolation and Borylation of Arylazo Sulfones with Thiols and B2pin2

An efficient electrochemical synthesis approach of various unsymmetrical thioethers and arylboronates has been developed. Bench stable arylazo sulfones were used as radical precursors for carbon-heteroatom bond formation under electrochemical conditions. Moreover, the scalability of this approach was evaluated by performing the electrochemical thiolation and borylation of arylazo sulfones with thiols and B2pin2 on a gram scale. This protocol not only avoided the use of stoichiometric oxidants, metal catalysts, activating agents and even added bases, but also exhibited favorable functional group tolerance. (Figure presented.).

Sulfoxide and Sulfone Synthesis via Electrochemical Oxidation of Sulfides

The oxidation of diaryl sulfides and aryl alkyl sulfides to the corresponding sulfoxides and sulfones under electrochemical conditions is reported. Sulfoxides are selectively obtained in good yield under a constant current of 5 mA for 10 h in DMF, while sulfones are formed as the major product under a constant current of 10 or 20 mA for 10 h in MeOH. The oxygen of both the sulfoxide and sulfone function is derived from water.

Photocatalytic Activity of Ruthenium(II) Complex with 1,10-Phenanthroline-3,8-dicarboxylic Acid in Aerobic Oxidation Reactions

Abstract: Mixed-ligand ruthenium(II) complex with 2,2′-bipyridine and 1,10-phenanthroline-3,8-dicarboxylic acid with the composition [Ru(phen-C)(bpy)2]Cl2·5H2O (bpy = 2,2′-bipyridine, phen-C = 1,10-phenantroline-3,8-dicarboxylic acid) has been synthesized and characterized by spectral data. The complex has been tested as photocatalyst in aerobic oxidation reactions, including transformation of arylboronic acids to phenols, primary amines to imines, and sulfides to sulfoxides in aqueous medium. The possibility of regeneration of the catalyst in the oxidation of sulfides has been demonstrated.

Synthesis of an anthraquinone-containing polymeric photosensitizer and its application in aerobic photooxidation of thioethers

Work on the synthesis of a polymeric photosensitizer and its application in the photooxidation of thioethers is reported herein. Firstly, the polymeric photosensitizer was designed and synthesized by the reaction of anthraquinone-2-carbonyl chloride (AQ-2-COCl) with poly(2-hydroxyethyl methacrylate) (PHEMA). Then, the visible light-induced photooxidation of thioethers under aerobic conditions was investigated. The results revealed that the reaction yielded sulfoxides highly chemoselectively in excellent yields with good substrate tolerance. Importantly, AQ-PHEMA could be easily recovered and reused more than 20 times without significant loss of the catalytic activity.

Synthesis and nano-Pd catalyzed chemoselective oxidation of symmetrical and unsymmetrical sulfides

A highly chemoselective, efficient and nano-Pd catalyzed protocol for the rapid construction of sulfoxides and sulfones via the oxidation of symmetrical and unsymmetrical sulfides using H2O2 as an oxidant has been developed, respectively. The ready availability of starting materials, easy recovery and reutilization of the catalyst, wide substrate scope, and high yields make this protocol an attractive alternative. The process also involves the metal-free and microwave-promoted synthesis of symmetrical diarylsulfides, and FeCl3-mediated preparation of symmetrical diaryldisulfides through the reaction of arenediazonium tetrafluoroborates with Na2S·9H2O as a sulfur source. In addition, unsymmetrical sulfides were generated via the K2CO3-mediated reaction of arenediazonium tetrafluoroborates with symmetrical disulfides.

Catalyst-free visible-light-initiated oxidative coupling of aryldiazo sulfones with thiols leading to unsymmetrical sulfoxides in air

A facile and efficient visible-light-driven method has been developed to construct sulfoxides via oxidative coupling of aryldiazo sulfones with thiols using the O2 in air as the oxidant. This reaction could be performed at room temperature under catalyst- and additive-free conditions. The present methodology offers a mild and environmentally benign approach to obtain a library of sulfoxides in good yields with favorable functional group tolerance.

Method for preparing visible light promoted asymmetric sulfoxide compound

The invention belongs to the field of organic synthetic chemistry, particularly relates to a preparation method of an asymmetric sulfoxide compound, and particularly discloses a method for synthesizing the asymmetric sulfoxide compound based on visible light catalysis. A compound shown in the formula I and a compound shown in the formula II are added to a reactor, a mixture of an organic solvent and water is added as a reaction solvent, the reactor is connected to air, under the irradiation of visible light, a reaction at a room temperature is performed for 16-40 hours; and after a detection reaction of a TLC thin layer chromatography plate is completed, pure water is added, then the extraction is performed, extract liquid is combined and dried, the extract liquid is concentrated and purified to obtain a compound shown in the formula III, and the compound is the asymmetric sulfoxide compound. The reaction conditions are mild, energy is clean, a strong oxidant is not needed, the safetyof the reaction is improved, the pollution caused by using a metal reagent is avoided, and the reaction cost is saved.