60301-03-3

Upstream product

• 71257-51-7 3-pyridyl phenyl sulfoxide 
• 16750-63-3 2-methoxyphenylmagnesium bromide 
• 108770-97-4 4-pyridyl phenyl sulfoxide 
• 14065-22-6 1-methoxy-2-(phenylthio)benzene 
• 529-28-2 4-iodoanisol 
• 670-98-4 methyl benzenesulfinate 
• 100-66-3 methoxybenzene 
• 13920-94-0 bis(2-methoxyphenyl)disulfide 
• 492-95-5 2-methoxyphenyldiazonium tetrafluoroborate 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 66003-76-7 Diphenyliodonium triflate 
• 108-98-5 thiophenol 
• 591-50-4 iodobenzene 
• 7217-59-6 2-Methoxybenzenethiol 

Downstream Products

• 1375487-85-6 1,4-diiodotetrafluorobenzene/phenyl 2-methoxyphenyl sulfoxide 1:1 cocrystal 

Relevant academic research and scientific papers

Modulation of photochemical oxidation of thioethers to sulfoxides or sulfones using an aromatic ketone as the photocatalyst

We have developed an eco-friendly and chemo-selective photocatalytic synthesis of sulfoxides or sulfones via oxidation of sulfides (thioethers) at ambient temperature using air or O2 as the oxidant. An inexpensive thioxanthone was used as the photocatalyst. Our method offers excellent chemical yields and good functional group tolerance. The hydrogen bonding between hexafluoro-2-propanol (HFIP) and sulfoxides may play an important role in minimizing the over-oxidization of sulfoxides.

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.

Sulfoxide synthesis from sulfinate esters under Pummerer-like conditions

A facile synthetic method for the preparation of allyl sulfoxides byS-allylation of sulfinate esters proceeds through sulfonium intermediates without [3,3]-sigmatropic rearrangement and further Pummerer-type reactions of the resulting allyl sulfoxides. On the basis of the plausible reaction mechanism involving sulfonium salt intermediates,S-alkynylation andS-arylation were also accomplished.

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.

Transition-Metal-Free Arylations of In-Situ Generated Sulfenates with Diaryliodonium Salts

A transition-metal-free arylation of sulfenate anions generated from β-sulfinyl esters with diaryliodonium salts was developed. In this process, a new C-S bond is formed under mild reaction conditions providing a wide range of S,S-diaryl and S-alkyl S-aryl sulfoxides.

Visible-Light-Driven Silver-Catalyzed One-Pot Approach: A Selective Synthesis of Diaryl Sulfoxides and Diaryl Sulfones

An efficient one-pot approach for the synthesis of diaryl sulfoxides and diaryl sulfones using aryl thiols and aryl diazonium salts was developed. The use of a visible-light-driven silver catalysis and the subsequent singlet-oxygen-induced oxidation enabled selective synthesis of sulfoxides and sulfones in the absence of a photocatalyst. The reactions were carried out under mild reaction conditions; the desired products were obtained under air atmosphere at room temperature.

Tert-Butyl Sulfoxides: Key Precursors for Palladium-Catalyzed Arylation of Sulfenate Salts

The present report describes an efficient and clean generation of sulfenate salts (R1SO-) by pyrolysis of readily available tert-butyl sulfoxides to give sulfenic acids (R1SOH) and traceless isobutene, followed by hydrogen abstraction with a weak inorganic base (K3PO4). The relevance of this process was exemplified through an in situ palladium-catalyzed cross-coupling reaction with aryl halides/triflates leading to aryl sulfoxides. The operationally simple C-S bond-forming protocol developed uses Pd(dba)2 as catalyst and Xantphos as ligand in toluene or a toluene/H2O mixture. Further extensions include the use of di-tert-butyl sulfoxide as an equivalent for sulfur monoxide dianion (SO2-) and the development of diastereoselective versions in the [2.2]paracyclophane and biaryl series.

Investigation of steric and electronic effects in the copper-catalysed asymmetric oxidation of sulfides

Steric and electronic effects in the copper-catalysed asymmetric oxidation of aryl benzyl, aryl alkyl and alkyl benzyl sulfides have been investigated. The presence of an aryl group directly attached to the sulfur is essential to afford sulfoxides with high enantioselectivities, with up to 97% ee for 2-naphthyl benzyl sulfoxide, the highest enantioselectivity achieved to date for copper-catalysed asymmetric sulfoxidation. In contrast, the benzyl substituent can be replaced by sterically comparable groups with no effect on enantioselectivity. Copper-mediated oxidation of substituted aryl benzyl sulfides display modest steric and electronic effects resulting in comparable or lower enantioselectivities to those obtained with the unsubstituted benzyl phenyl sulfide.

Methyl sulfinates as electrophiles in friedel-crafts reactions. Synthesis of aryl sulfoxides

The Friedel-Crafts reaction of methyl alkyl- and arylsulfinates with aromatic systems, activated by one or more electron-donating substituents (OH, OMe, NHR, NR2), provides alkyl aryl and diaryl sulfoxides under mild conditions and in moderate to good yields. The very high regioselectivity usually observed in these sulfinylation reactions is rationalized on the basis of a Wheland intermediate having a trigonal bypyramidal structure in which steric and electronic interactions are significant factors strongly destabilizing the attack to the ortho positions.

A NEW APPROACH FOR PREPARATION OF ATROPISOMERS OF ARYLPYRIDYLS VIA CROSS-COUPLING REACTIONS OF ARYL 2-(3-SUBSTITUTED)PYRIDYL SULFOXIDES WITH GRIGNARD AND ORGANOLITHIUM REAGENTS

The cross-coupling reactions of phenyl 2-(3-substituted)pyridyl sulfoxides with 2-methoxyphenyl- and 1-(2-methoxy)naphthyl Grignard and 2-phenoxyphenyl lithium reagents afforded atropisomers of arylpyridyl derivatives in good yields which undergo thermal epimerization.