34917-41-4

Upstream product

• 13865-49-1 [2-(phenylsulfanyl)ethyl]benzene 
• 108-98-5 thiophenol 
• 103-63-9 1-phenyl-2-bromoethane 
• 108-86-1 bromobenzene 
• 4410-99-5 2-mercaptophenylethane 
• 100-42-5 styrene 

Downstream Products

• 29626-90-2 1-chloro-2-phenylethyl phenyl sulfoxide 
• 31268-22-1 (1-Brom-2-phenylethyl)-phenyl-sulfoxid 
• 2643-39-2 1-Benzenesulphonyl-2-bromo-2-phenylethane 
• 59176-57-7 (Z)-1-phenylthio-1-trimethylsilyl-2-phenylethylene 
• 62762-23-6 (E)-1-phenylthio-1-trimethylsilyl-2-phenylethylene 
• 104306-39-0 methyl 2-methyl-4-phenyl-3-(phenylthio)butyrate 
• 21461-90-5 (meso)-1,2-bis(phenylsulfinyl)ethane 
• 114263-63-7 C₁₄H₁₃FS 
• 98750-73-3 C₁₄H₁₂Cl₂S 
• 100-42-5 styrene 
• 882-33-7 diphenyldisulfane 
• 54905-12-3 (2-phenylethane-1,1-diyl)bis(phenylsulfane) 
• 16619-61-7 1-phenyl-2-phenylthioethene 
• 13865-49-1 [2-(phenylsulfanyl)ethyl]benzene 

Relevant academic research and scientific papers

Palladium/PC-Phos-Catalyzed Enantioselective Arylation of General Sulfenate Anions: Scope and Synthetic Applications

Herein we reported an efficient palladium-catalyzed enantioselective arylation of both alkyl and aryl sulfenate anions to deliver various chiral sulfoxides in good yields (up to 98%) with excellent enantioselectivities (up to 99% ee) by the use of our developed chiral O,P-ligands (PC-Phos). PC-Phos are easily prepared in short steps from inexpensive commercially available starting materials. The single-crystal structure of the PC4/PdCl2 showed that a rarely observed 11-membered ring was formed via the O,P-coordination with the palladium(II) center. The salient features of this method include general substrate scope, ease of scale-up, applicable to the late-stage modification of bioactive compounds, and the synthesis of a marketed medicine Sulindac.

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.

Sulfoxidation of alkenes and alkynes with NFSI as a radical initiator and selective oxidant

Sulfoxides are important functional molecules. We develop a short-route (one-pot) synthesis of this class of molecules by reacting thiols with alkenes or alkynes under mild and metal-free conditions. N-Fluorobenzenesulfonimide (NFSI) is used to play dual roles: as a radical initiator for a thiol-ene/-yne reaction to form sulfide adducts, and as efficient oxidant for conversion of the sulfides formed in situ to sulfoxides. Over-oxidation of the sulfoxides to sulfones is avoided in our approach.

Visible-light-induced selective synthesis of sulfoxides from alkenes and thiols using air as the oxidant

A highly selective synthesis of sulfoxides from alkenes and thiols was established by visible-light photoredox catalysis at room temperature. This metal-free transformation protocol, which uses inexpensive Rose Bengal as the photocatalyst and air as the green oxidant, opens a new door toward the facile and practical construction of sulfoxides.

Green Organocatalytic Oxidation of Sulfides to Sulfoxides and Sulfones

A highly efficient synthetic methodology towards the selective synthesis of sulfoxides and sulfones is reported using a cheap and green organocatalytic method. Starting from sulfides and using 2,2,2-trifluoroacetophenone as the organocatalyst and H2O2 as the oxidant, the high-yielding preparation of sulfoxides or sulfones is described, being dependent on the reaction conditions.

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.

Palladium-Catalyzed Arylation of Alkyl Sulfenate Anions

A unique palladium-catalyzed arylation of alkyl sulfenate anions is introduced that affords aryl alkyl sulfoxides in high yields. Due to the base sensitivity of the starting sulfoxides, sulfenate anion intermediates, and alkyl aryl sulfoxide products, the use of a mild method to generate alkyl sulfenate anions was crucial to the success of this process. Thus, a fluoride triggered elimination strategy was employed with alkyl 2-(trimethylsilyl)ethyl sulfoxides to liberate the requisite alkyl sulfenate anion intermediates. In the presence of palladium catalysts with bulky monodentate phosphines (SPhos and Cy-CarPhos) and aryl bromides or chlorides, alkyl sulfenate anions were readily arylated. Moreover, the thermal fragmentation and the base promoted elimination of alkyl sulfoxides was overridden. The alkyl sulfenate anion arylation exhibited excellent chemoselectivity in the presence of functional groups, such as anilines and phenols, which are also known to undergo palladium catalyzed arylation reactions.

SnO 2 nanoparticles: Preparation and evaluation of their catalytic activity in the oxidation of aldehyde derivatives to their carboxylic acid and sulfides to sulfoxide analogs

A variety of aromatic and aliphatic aldehydes were converted to the corresponding carboxylic acid derivatives with 30% H2O2 and tert-butyl hydroperoxide as the oxidant in the presence of a catalytic amount of SnO2 nanoparticles as a precursor. These nanoparticles were also used for the efficient catalytic oxidation of sulfides to sulfoxides using 30% H2O2. The present methodology offers several advantages such as applicability to a wide range of aldehydes/sulfides, convenient work-up, mild reaction conditions as well as good yields and reasonable time of the reactions. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

Reaction of singlet oxygen with some benzylic sulfides

Product distribution, total quenching rate (kT), and rate of chemical reaction (kr) with singlet oxygen have been determined for some alkyl, benzyl, α-methylbenzyl, and cumyl sulfides. Their contributions depend on the steric hindering around the sulfur atom. In protic solvents, the sulfoxide is the main product via a hydrogen-bonded persulfoxide. In apolar solvents, intramolecular α-H abstraction leads to oxidative C-S bond cleavage, with varying efficiency. The behavior of sulfides is compared to that of alkenes and amines.

Selective oxidation of sulfides to sulfoxides using 30% hydrogen peroxide catalyzed with a recoverable silica-based tungstate interphase catalyst

(Chemical Equation Presented) Various types of aromatic and aliphatic sulfides are selectively oxidized to sulfoxides and sulfones in good to excellent yields using 30% H2O2 in the presence of catalytic amounts of a novel recoverable silica-based tungstate interphase catalyst at room temperature. The catalyst can be recovered and reused for at least eight reaction cycles under the described reaction conditions without considerable loss of reactivity.