5324-90-3

Upstream product

• 455-16-3 p-toluenesulfonyl fluoride 
• 594-19-4 tert.-butyl lithium 
• 56583-96-1 tert-butylcopper(I) 
• 7439-10-3 tert-butyl 4-methylphenyl sulfide 
• 37972-90-0 2,6-Dibrom-4-thiocresol 
• 62261-16-9 tert.-Butyl-2,6-dibrom-4-tolylsulfid 
• 106-45-6 para-thiocresol 
• 6968-24-7 2,6-Dibromo-4-methylaniline 
• 62261-18-1 tert-Butyl-(2,6-dibromo-4-methylphenyl)sulfone 

Downstream Products

• 69649-29-2 tert.Butyl-2-Iodo-4-tolylsulfon 
• 102212-05-5 benzyl p-neopentylphenyl sulfone 
• 62261-22-7 C₁₁H₁₄Li₂O₂S 
• 66131-57-5 C₇H₅Li 

Relevant academic research and scientific papers

Titanium-Catalyzed, Asymmetric Sulfoxidation of Alkyl Aryl Sulfides with Optically Active Hydroperoxides

The Ti-catalyzed, asymmetric oxidation of alkyl aryl sulfides by enantiomerically pure hydroperoxides (ee >99%) has been examined. Enantioselectivities with ee values up to ca. 80% were achieved for the oxygen transfer from (S)-(-)-1-phenylethyl hydroperoxide 2a to methyl phenyl and methyl p-tolyl sulfide 1a in CCl4 as solvent, but with much overoxidation to the corresponding sulfone 4. Detailed mechanistic studies showed that the enantioselectivity of the sulfide 1a oxidation results from a combination of a rather low (ee values >20%) asymmetric induction in the sulfoxidation and an effective kinetic resolution (ee values ca. 80% at 85% sulfide conversion) of the sulfoxide 3a by enantioselective oxidation to the sulfone 4a. The overoxidation (loss of chemoselectivity) is due to sulfoxide coordination to the Ti metal to generate a template in which the oxygen atom is intramolecularly transferred from the bound and activated, optically active hydroperoxide to the ligated sulfoxide in a stereocontrolled manner.

Sulfonylation of Organometallic Reagents with Arenesulfonyl Fluorides: A Simple One-Step Synthesis of Sulfones

Sulfonylation of organometallic reagents was accomplished with arenesulfonyl fluorides to provide a wide variety of alkylaryl- and diaryl sulfones.Organolithium and diorganocopper lithium reagents react smoothly with arenesulfonyl fluorides to give sulfones in high yields.Alkyl Grignard reagents often lead to mixtures of monosulfonylated and disulfonylated products.However, allylmagnesium chloride and phenylmagnesium chloride provide the corresponding sulfones in excellent yields.Organocopper reagents were also found to yield sulfones upon treatment with arenesulfonyl fluorides.By utilizing this methodology, synthetically useful alkyl, (trimethylsilyl)methyl, and allyl sulfones are easily prepared in high yields.