3972-22-3

Upstream product

• 2633-66-1 2-mesitylmagnesium bromide 
• 108-67-8 1,3,5-trimethyl-benzene 

Downstream Products

• 392-69-8 1-fluoro-2,4,6-trimethylbenzene 
• 82039-63-2 (+)-(R)-isopropyl (2,4,6-trimethylphenyl) sulfoxide 
• 82039-64-3 (-)-(S)-isopropyl (2,4,6-trimethylphenyl) sulfoxide 
• 5324-71-0 2,2',4,4',6,6'-hexamethyldiphenyl sulfide 
• 129315-29-3 isobutyl (2,4,6-trimethylphenyl)sulfoxide 
• 50458-30-5 C₂₇H₃₂OS 

Relevant academic research and scientific papers

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.

Synthesis of o-Aryloxy Triarylsulfonium Salts via Aryne Insertion into Diaryl Sulfoxides

The aryne insertion into "S-O" bond has been validated recently. This technology is elusively applied to the synthesis of thioethers. In contrast to the reported cases, the reaction described furnished o-aryloxy triarylsulfonium salts, in lieu of thioethe

Desymmetrization of prochiral diaryl sulfoxides by an asymmetric sulfoxide-magnesium exchange

The first desymmetrizations of prochiral diaryl sulfoxides 1 by an asymmetric sulfoxide-magnesium exchange reaction are reported. The respective substrate (1), iPr2Mg, and the dilithium salt of (S)-BINOL (which was prepared in situ) provided (S)-configured aryl isopropyl sulfoxides 2 in up to 91 % yield and with up to 91 % ee. (S)-BINOL was re-isolable in 98 % yield. Copyright

Polystyrene and silica gel-supported, AlCl3-catalyzed preparation of diaryl sulfoxides from arenes and thionyl chloride

A simple, chemoselective, and efficient method has been developed for direct conversion of arenes to symmetrical diaryl sulfoxides using thionyl chloride in the presence of a catalytic amount of cross-linked polystyrene-supported aluminium chloride (Ps-AlCl3) and silica gel-supported aluminium chloride (SiO2-AlCl3). These solid acid catalysts are stable and can be easily recovered and reused without appreciable change in their efficiency. Copyright Taylor & Francis Group, LLC.

Lithium/Sodium Perchlorate Catalyzed Synthesis of Symmetrical Diaryl Sulfoxides

Synthesis of diaryl sulfoxides from aromatics and thionyl chloride catalyzed by LiClO4/NaClO4 at room temperature is described. Mild reaction conditions, simple work-up, inexpensive and easily available catalysts are important and attractive features of this method.

An ionic liquid-mediated expeditious route to the syntheses of diaryl sulfoxides

A fast and efficient protocol is proposed for the synthesis of diaryl sulfoxides in the ionic liquid 1-butyl-3-methylimidazolium chloroaluminate, [bmim]Cl·AlCl3, N=0.67, by employing arenes and thionyl chloride. The ionic liquid plays a dual role of Lewis acid catalyst and solvent, under ambient conditions, offering good yields of the product. The influence of the Lewis acidity of the ionic liquid on the extent of conversion is studied.

Trifluoromethanesulfonic acid catalyzed preparation of symmetrical diaryl sulfoxides from arenes and thionyl chloride

The preparation of symmetrical diaryl sulfoxides from thionyl chloride and arenes catalyzed by trifluoromethanesulfonic acid is described. The reaction is characterized by its mildness, high yields, selectivity, and ease of workup.

Reaction of Simple Arenes with FSO3H*SbF5/SO2: One-Pot Synthesis of Aromatic Sulfoxides. Mechanistic Aspects and Synthetic Utility

In a simple one-pot reaction, mono-, di-, tri-, and polyalkylbenzenes, isomeric alkylhalobenzenes, and fluoro-, (trifluoromethyl)-, and 1,3,5-trifluorobenzene were converted to their corresponding diaryl sulfoxides with FSO3H*SbF5 (1:1) (magic acid)/SO2.Dependency of the yields on the acidity (H0) and the arene structure was demonstrated.Reduction of the formed sulfoxide was also observed as a minor pathway to give diaryl sulfide.The reduction is superacid-catalyzed, and protonated sulfoxides are the key intermediates en route to sulfides.Protonation of several functionalized diaryl sulfoxides was also studied in magic acid/SO2 under stable ion conditions.Unlike the parent diphenyl sulfoxide, which is S-protonated, alkyl-, fluoro-, and trifluoromethyl-substituted diaryl sulfoxides O-protonate to give long-lived sulfoxonium ions.The proposed mechanism for the arene/superacid/SO2 system involves sulfination of the arenium ions, O-protonation of the resulting sulfinic acid, dehydration of the oxonium ion "ArSO+" and arylation.In the absence of SO2, the fluorosulfonation, ionization, arylation path becomes dominant.The scope of the reaction is sufficiently broad to be synthetically useful.The methodology is also applicable to unsymmetrical (mixed) diaryl sulfoxides.