681006-46-2

Upstream product

• 6873-93-4 1-[(4-methylphenyl)sulfinyl]piperidine 
• 98-83-9 isopropenylbenzene 
• 106-45-6 para-thiocresol 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 536-57-2 p-toluene sulfinic acid 

Relevant academic research and scientific papers

Copper(II) Acetate-Catalyzed Hydroxysulfenylation-Initiated Lactonization of Unsaturated Carboxylic Acids with Oxygen as Oxidant and Oxygenation Reagent

A copper(II) acetate-catalyzed aerobic thiolation of C=C double bonds, oxygenation, and intramolecular cyclization reactions of unsaturated carboxylic acids with thiols has been explored. The reaction proceeds through a new hydroxysulfenylation-initiated lactonization pathway with carboxyl as electrophilic group, which provides an efficient access to assembly highly valuable thio-substituted lactone derivatives with good yields under mild conditions. Several control experiments, as well as an isotope labelling experiment disclose that oxygen acts as both oxidant and reactant being transferred into the final product. The mechanistic studies support the discovery of a new strategy through difunctionalization of alkenes based on unsaturated carboxylic acids to construct the diversely substituted lactones. (Figure presented.).

Auto-oxidative hydroxysulfenylation of alkenes

One-pot auto-oxidation mediated hydroxysulfenylation of electron-deficient and electron-rich olefins with phenthiols was explored. The method illustrates a selective and convenient synthesis of complex β-hydroxysulfides using O2 as both the oxidant and the oxygen source under mild transition-metal-free conditions. The application of this new methodology to the gram-scale synthesis of anti-cancer drug bicalutamide has been accomplished in a two-step sequence with 71% overall yield. A plausible radical involved mechanism is proposed.

A α-hydroxy-P-phenylene sulfide and its preparation method and application

The invention discloses alpha-hydroxysulfide and a preparation method and application thereof. The alpha-hydroxysulfide has a structure formula as shown in formula I. The polysubstituted alpha-hydroxysulfide structure can be constructed by direct use of industrial raw materials thiophenol and derivatives thereof and the like. The method realizes production of the alpha-hydroxysulfide by use of very cheap metal Cu and a simple organic carboxylic acid used as a promoter and direct use of oxygen to oxidize industrial raw materials thiophenol and derivatives thereof for oxidation hydroxylation reaction with olefins. According to the method, oxygen is used as an oxidant, atomic economy property is high, and the method is environmental friendly. The method is simple in operation, direct high-yield synthesis of alpha-hydroxysulfide compounds can be achieved only by one step, the product is easy to purify, and the method is groundbreaking, is not available in other traditional organic synthesis, and has optimistic application prospects.

Hydroxysulfenylation of electron-deficient alkenes through an aerobic copper catalysis

A copper-catalyzed hydroxysulfenylation of α,β-unsaturated esters/amides is reported. The method presents a selective and efficient synthesis of β-hydroxysulfides bearing electron-withdrawing groups. The synthetic utility of this method is demonstrated by the concise synthesis of the anticancer drug bicalutamide.

p-Tolylsulfinyl Amides: Reagents for Facile Electrophilic Functionalization of Olefins

A variety of olefins were found to react with sulfinyl amides in the presence of POCl3 to give β-chlorosulfides and β-hydroxysulfides in good yields. In the absence of nucleophiles, p-tolylsulfinyl amides were found to react with olefins with the formation of allylsulfoxides.