20663-33-6

Upstream product

• 766-85-8 3-methoxy-1-iodobenzene 
• 1858-86-2 Ethyl p-toluenesulfinate 
• 911820-09-2 3-[(4-methylphenyl)sulfinyl]propanoic acid tert-butyl ester 
• 10381-71-2 p-tolyl allyl sulfoxide 
• 2398-37-0 3-methoxyphenyl bromide 
• 50444-99-0 (1R,2S,5R)-menthyl-(S)-p-toluenesulfinate 
• 91796-57-5 (1S,2R,5S,R_S)-(+)-Menthyl toluene-p-sulfinate 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 106-38-7 para-bromotoluene 
• 274928-75-5 1-methanesulfinyl-3-methoxy-benzene 

Downstream Products

• 149452-90-4 3-methoxyphenyl 4-methylphenyl sulfone 
• 1194840-60-2 (S(S))-(-)-2-iodo-1-methoxy-3-(p-tolylsulfinyl)benzene 
• 1194840-66-8 (S)-(-)-2',2-dimethoxy-6-(p-tolylsulfinyl)biphenyl 
• 1194840-64-6 (S)-2-methoxy-2'-methyl-6-(p-tolylsulfinyl)-1,1'-biphenyl 

Relevant academic research and scientific papers

Atropo-diastereoselective coupling of aryllithiums and arynes — variations around the chiral auxiliary

The atropo-selective coupling of in situ generated arynes and aryllithiums bearing various chiral auxiliaries ortho to lithium (tert-butylsulfoxide, para-tolylsulfoxide, tartrate-derived chiral diethers and oxazolines) is described. Chiral oxazolines showed the best results in terms of yields of coupling products. Different reaction parameters like the nature of the aryne precursor, the oxazoline, the alkyllithium base or the solvent revealed to be crucial for obtaining good yields and for diastereoselection.

Synthesis of axially chiral biaryls through sulfoxide-directed asymmetric mild C-H activation and dynamic kinetic resolution

A mild and robust direct C-H functionalization strategy has been applied to the synthesis of axially chiral biaryls. Such an efficient and stereoselective transformation occurs through an original dynamic kinetic resolution pathway enabling the conversion of diastereomeric mixtures of non-prefunctionalized substrates into atropisomerically pure, highly substituted biaryl scaffolds. The main feature of this transformation is the use of an enantiopure sulfoxide as both chiral auxiliary and traceless directing group. The potential of newly synthesized biaryls as valuable building blocks is further illustrated.

Atropodiastereoselective C-H olefination of biphenyl p-tolyl sulfoxides with acrylates

A stereoselective method for the synthesis of axially chiral biaryl scaffolds by C-H bond functionalization was accomplished using chiral sulfoxide both as the directing group enabling the regioselective activation of a C-H bond and as the chiral auxiliary generating an asymmetric environment in the coordination sphere of the metal complex. We have demonstrated the directing ability of the p-tolylsulfinyl group in promoting the Pd(II)-catalyzed C-H olefination of biphenyls.

Direct S-arylation of unactivated arylsulfoxides using [Pd(IPr*)(cin) Cl]

The direct S-arylation of unactivated arylsulfoxides catalyzed by [Pd(IPr*)(cin)Cl] is described. Several arylmethylsulfoxides were coupled to various aryl halides in moderate to good yields (17 examples, 34-85%). Scope, limitations, and reaction mechanis

Aryl sulfoxides from aliyi sulfoxides via [2,3]-sigmatropic rearrangement and domino Pd-catalyzed generation/ arylation of sulfenate anions

(Figure presented) Allylic sulfoxides, via [2,3]-sigmatropic rearrangement and oxidative addition of the resulting allylic sulfonate esters to Pd(0), are found to be excellent precursors of sulfenate anions. This hitherto unknown reactivity is applied in a new Pd(0)-catalyzed domino sequence involving sulfonate anion generation followed by arylation to afford aryl sulfoxides.

Highly effective and diastereoselective synthesis of axially chiral bis-sulfoxide ligands via oxidative aryl coupling

Figure presented A series of axially chiral bis-sulfoxide ligands have been efficiently synthesized via oxidative coupling with high diastereoselectivities. The axial chirality is well controlled by the tert-butylsulfinyl or the p-tolylsulfinyl group. The

Axial chirality control during suzuki-miyaura cross-coupling reactions: The tert-Butylsulfinyl group as an efficient chiral auxiliary

An efficient route to a new family of axially chiral biaryl ligands by a Suzuki-Miyaura cross-coupling reaction between ortho,ortho'-disubstituted aryl iodides bearing in ortho position a tert-butyl or p-tolylsulfinyl group and ortho-substituted phenyl boronic acids or esters is described. The comparison between the t-BuSO and p-TolSO groups as chiral controllers is reported. The modularity of the approach is demonstrated by the preparation of a variety of enantiopure axially chiral mixed S/N and S/P ligands.

Enantioselective synthesis of aryl sulfoxides via palladium-catalyzed arylation of sulfenate anions

Arylation of various sulfenate anions generated from β-sulfinyl esters by retro-Michael reaction in the presence of palladium(0) and enantiopure ligands gave the corresponding aryl sulfoxides in enantio-enriched form. The Josiphos-type ligand (R)-(S)-PPF-

The first stereoselective Pd-catalyzed addition of boronic acids onto aldehydes

The coupling reaction between 2-p-tolylsulfinyl benzaldehyde and substituted boronic acids catalyzed by Pd2(dba)3·CHCl3 proceeds in a stereoselective manner, demonstrating the efficiency of the sulfinyl group as a chiral i

Aryl sulfoxides via palladium-catalyzed arylation of sulfenate anions

(Chemical Equation Presented) Palladium-catalyzed arylation of sulfenate anions generated from β-sulfinyl esters can take place under biphasic conditions. This hitherto unknown reaction provides a simple, mild, and efficient route to aryl sulfoxides in good yields. The development of a new pseudo-domino type I procedure involving a sulfinylation followed by a Mirozoki-Heck coupling is also described.