139286-41-2

Upstream product

• 100-42-5 styrene 
• 75-66-1 2-methylpropan-2-thiol 
• 62252-51-1 2-phenylethyl tert-butyl sulfide 
• 6163-64-0 tert-butyl methyl sulphide 
• 90878-19-6 phenethylmagnesium chloride 
• 126494-96-0 2,2-diphenyl-1,2-dihydroxypropyl 2-O-tert-butylsulfinate 

Downstream Products

• 1256268-29-7 diphenylstyrylphosphine borane 
• 120982-93-6 (S)-4-((S)-2-Methyl-propane-2-sulfinyl)-5-phenyl-pentanoic acid methyl ester 
• 120982-93-6 (R)-4-((S)-2-Methyl-propane-2-sulfinyl)-5-phenyl-pentanoic acid methyl ester 
• 120982-95-8 (3S,4S)-4-((S)-2-Methyl-propane-2-sulfinyl)-3,5-diphenyl-pentanoic acid methyl ester 
• 120982-95-8 (3S,4S)-4-((R)-2-Methyl-propane-2-sulfinyl)-3,5-diphenyl-pentanoic acid methyl ester 
• 120982-95-8 4-(2-Methyl-propane-2-sulfinyl)-3,5-diphenyl-pentanoic acid methyl ester 

Relevant academic research and scientific papers

Fullerene soot and a fullerene nanodispersion as recyclable heterogeneous off-the-shelf photocatalysts

Metal-free heterogeneous photocatalysis, which requires no prior catalyst immobilization or chemical modification and can operate in green solvents, represents a highly-sought after, yet currently still underdeveloped, synthetic method. In this report we present a comparative study which aims to evaluate the use of unmodified fullerene soot and a fullerene nanodispersion as non-soluble and quasi-soluble carbon-based photocatalysts, respectively, for sulfide oxidation and other transformations using oxygen as an oxidant in ethanol. A wide range of sulfoxides were successfully prepared with good yields and chemoselectivity using a very low catalyst loading. The fullerene soot photocatalyst is easily recovered and shows excellent stability of the catalytic properties. The reaction was shown to proceed via a singlet oxygen pathway and has a high selectivity for aliphatic sulfides, whereas the oxidation of thioanisoles can be accomplished using an amine mediated electron transfer mechanism. The applicability of the fullerene nanodispersion as a general purpose photocatalyst was demonstrated in radical cyclization, boronic acid oxidation and imine formation reactions.

Chemoselective α-sulfidation of amides using sulfoxide reagents

The direct α-sulfidation of tertiary amides using sulfoxide reagents under electrophilic amide activation conditions is described. Employing convenient and readily available reagents, selective functionalization takes place to generate isolable sulfonium

Visible-light-activated selective synthesis of sulfoxides via thiol-ene/oxidation reaction cascade

A convenient, highly selective and metal-free synthesis of sulfoxides from alkenes and thiols using NHPI as an inexpensive and reusable organophotoredox catalyst is reported. The protocol involves radical thiol-ene/oxidation reaction cascade and utilizes visible light and air (O2) as inexpensive, readily available, non-toxic and eco-sustainable reagents to afford up to 96% yields of the product at room temperature.

Thiol-ene/oxidation tandem reaction under visible light photocatalysis: Synthesis of alkyl sulfoxides

The photocatalyzed synthesis of sulfoxides from alkenes and thiols has been carried out using Eosin Y. This is a metal-free method which uses a low catalyst loading, atmospheric oxygen as the oxidant, and visible light conditions (green light). A mechanism has been proposed that is consistent with the experimental results.

Acid-Catalyzed Oxidative Addition of Thiols to Olefins and Alkynes for a One-Pot Entry to Sulfoxides

An oxidative variant of the thiol-ene reaction has been developed, achieving the direct addition of thiols to olefins to form sulfoxides. The reaction uses tert-butyl hydroperoxide as oxidant and methanesulfonic acid as catalyst. The latter is believed to catalyze the oxidation of the intermediate sulfide to the sulfoxide. No special precautions are necessary to exclude oxygen, yet the products are formed without oxidation at the β-position. Styrenes, acrylic acid derivatives, alkynes, and thiophenols gave the highest yields, while aliphatic olefins and thiols were less effective.

A General Route to Enantiomerically Pure Sulfoxides from a Chiral Sulfite

Enantiomerically pure cyclic chiral sulfite (S)-7 (trans stereochemistry) has been easily obtained in two steps from (S)-ethyl lactate.This compound was found to react cleanly with many organometallics to give crystalline sulfinates with high regioselecti