38644-97-2

Upstream product

• 637-59-2 1-Bromo-3-phenylpropane 
• 106-45-6 para-thiocresol 
• 300-57-2 allylbenzene 
• 501-52-0 3-Phenylpropionic acid 
• 657-84-1 sodium tosylate 
• 624-31-7 4-tolyl iodide 
• 4119-41-9 1-iodo-3-phenylpropan 
• 18241-64-0 S-p-tolyl butanethioate 
• 5285-74-5 4-tolyl thiocyanate 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 17041-81-5 p-tolyl benzenethiosulfonate 
• 23522-73-8 3-phenylpropionic acid 4-chlorophenyl ester 
• 726-26-1 phenyl 3-phenylpropanoate 
• 103-25-3 3-phenylpropanoic acid methyl ester 

Downstream Products

• 935662-15-0 (S_S)-3-phenylpropyl p-tolyl sulfoxide 
• 120982-92-5 1-methyl-4-(3-phenylpropylsulfinyl)benzene 

Relevant academic research and scientific papers

Copper-Catalyzed direct thioetherification of Alkyl Halides with S-Alkyl Butanethioate as Thiol transfer reagent

A new and convenient copper-catalyzed synthesis of alkyl sulfides has been accomplished using S-alkyl butanethioate as a thiol source. This catalytic protocol displayed a good functional groups tolerance and high efficiency. Both secondary and primary alkyl iodides can be used in this procedure. In addition, this method features operational simplicity and a wide substrate range, providing a complementary method for alkyl sulfide synthesis without requiring toxic thiols and noble metals.

Nickel-Catalyzed Reductive Thiolation of Unactivated Alkyl Bromides and Arenesulfonyl Cyanides

The cross-electrophile coupling between unactivated alkyl bromides with arenesulfonyl cyanides catalyzed by Ni(acac)2under reductive conditions to form unsymmetrical sulfides is developed. This approach for sulfide synthesis is practical, relies on available, unfunctionalized materials such as alkyl (pseudo)halides, and is scalable. This catalytic strategy provides a complementary method for the preparation of unsymmetrical alkyl-aryl sulfides under mild conditions with good functional group tolerance.

Redox-active benzimidazolium sulfonamides as cationic thiolating reagents for reductive cross-coupling of organic halides

Redox-active benzimidazolium sulfonamides as thiolating reagents have been developed for reductive C-S bond coupling. The IMDN-SO2R reagent provides a bench-stable cationic precursor to generate a portfolio of highly active N-S intermediates, which can be successfully applied in cross-electrophilic coupling with various organic halides. The employment of an electrophilic sulfur source solved the problem of catalyst deactivation and avoided odorous thiols, featuring practical conditions, broad substrate scope, and excellent tolerance.

Electroreductive Nickel-Catalyzed Thiolation: Efficient Cross-Electrophile Coupling for C?S Formation

Sulfur-containing molecules are of utmost topical importance towards the effective development of pharmaceuticals and functional materials. Herein, we present an efficient and mild electrochemical thiolation by cross-electrophile coupling of alkyl bromide

An Iodine-Mediated Hofmann-L?ffler-Freytag Reaction of Sulfoximines Leading to Dihydroisothiazole Oxides

A Hofmann-L?ffler-Freytag type cyclization reaction of S-aryl-S-phenylpropyl sulfoximines (and related derivatives) was developed. Using molecular iodine as the initiator under visible light a series of five-membered cyclic products was obtained in moderate to high yields. The approach represents a new strategy for the synthesis of dihydroisothiazole oxides and benzo[d]isothiazoles-1-oxides. (Figure presented.).

Metal–organic framework MOF-199-catalyzed direct and one-pot synthesis of thiols, sulfides and disulfides from aryl halides in wet polyethylene glycols (PEG 400)

A highly porous metal–organic frame work Cu3 BTC2 (copper(II)-benzene-1,3,5-tricarboxylate) that is known as MOF-199 was synthesized from the reaction of 1,3,5-benzenetricarboxylic acid and Cu(OAc)2·H2O by a solvothermal method and characterized by several techniques including FT-IR, XRD, EDX and scanning electron microscopy. The MOF-199 used as an efficient catalyst for one-pot synthesis of thiols by domino reactions of aryl halides and thiourea, and subsequently conversion to aryl alkyl sulfides and diaryl disulfides in polyethylene glycols (PEGs). A variety of aryl alkyl sulfides can be obtained in good to excellent yields in a relatively short reaction time and in the presence of the trace amount of catalyst. Also, the catalyst can be separated from the reaction mixture by decanting, and be reused without significant degradation in catalytic activity.

Acid/Phosphide-Induced Radical Route to Alkyl and Alkenyl Sulfides and Phosphonothioates from Sodium Arylsulfinates in Water

A newly developed aqueous system with acid and phosphide was introduced in which odorless and stable sodium arylsulfinates can in situ generate arylsulfenyl radicals. These radicals have high reactivity to react with alkynes, alkenes, and H-phosphine oxides for the synthesis of alkyl and alkenyl sulfides and phosphonothioates. The control experiments and quantum calculations are also performed to gain insights into the generation mechanism of arylsulfenyl radicals. Notably, the chemistry is free of thiol odors, organic solvents, and metals.

Indium-Catalyzed Reductive Sulfidation of Esters by Using Thiols: An Approach to the Diverse Synthesis of Sulfides

A new reductive preparation of unsymmetrical sulfides from esters and thiols in the presence of InI3 and either 1,1,3,3-tetramethyldisiloxane (TMDS) or PhSiH3 as the reductant was developed. This protocol was applied to not only benzoic acid esters that have a methoxy, methyl, chloro, bromo, iodo, or trifluoromethyl group on the aromatic ring but also aliphatic acid esters with either aromatic or aliphatic thiols. A reaction mechanism is proposed by using Hammett plot results and several control experiments. The reductive preparation of unsymmetrical sulfides from esters and thiols by using InI3 and either 1,1,3,3-tetramethyldisiloxane (TMDS) or PhSiH3 was developed. Several mechanistic studies support that the present transformation proceeds through O,S-and S,S-acetals as the reaction intermediates. TMDS = 1,1,3,3-tetramethyldisiloxane, R = aliphatic group.

Palladium(II)-catalyzed ortho -olefination of arenes applying sulfoxides as remote directing groups

A novel palladium-catalyzed ortho-C(sp2)-H olefination protocol has been developed by the use of sulfoxide as the directing group. Importantly, relatively remote coordination can be accessed to achieve the ortho olefination of benzyl, 2-arylethyl, and 3-arylpropenyl sulfoxide substrates, and the olefinated sulfoxide can be easily transformed to other functionalities.

Single-step thioetherification by indium-catalyzed reductive coupling of carboxylic acids with thiols

Direct thioetherification from a variety of aromatic carboxylic acids and thiols using a reducing system combined with InBr3 and 1,1,3,3-teramethyldisiloxane (TMDS) in a one-pot procedure is demonstrated. It was also found that a system combine