104368-08-3

Upstream product

• 455-16-3 p-toluenesulfonyl fluoride 
• 101-97-3 Ethyl 2-phenylethanoate 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 2882-19-1 ethyl 2-phenyl-2-bromoacetate 
• 4973-66-4 methyl thiotosylate 
• 22065-57-2 ethyl 2-phenyldiazoacetate 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 1028-19-9 1-(4'-methylbenzenesulfonyl)-1H-benzo[d][1.2.3]triazole 
• 10606-73-2 ethyl 2-chloro-2-phenylacetate 

Downstream Products

• 68342-73-4 phenyl-(toluene-4-sulfonyl)-acetic acid 
• 5395-20-0 1-methyl-4-(benzylsulfonyl)benzene 

Relevant academic research and scientific papers

Rh(ii)/phosphine-cocatalyzed synthesis of dithioketal derivatives from diazo compounds through simultaneous construction of two different C-S bonds

Rhodium(ii)/phosphine-cocatalyzed bis-sulfuration of α-diazocarbonyl compounds using thiosulfonates as the sulfenylating agent, which provided two sulfur-containing moieties, was developed via simultaneous inter- and intra-molecular C-S bond formation. This novel protocol provides a rapid synthetic route to dithioketal derivatives in moderate to good yields in an atom-economic process. The transformation is proposed to proceed through phosphine ylide formation followed by S(O2)-S bond cleavage and rearrangement.

Unexpected Role of p-Toluenesulfonylmethyl Isocyanide as a Sulfonylating Agent in Reactions with α-Bromocarbonyl Compounds

The reactions of p-toluenesulfonylmethyl isocyanide (TosMIC) with α-bromocarbonyl compounds leading efficiently to α-sulfonated ketones, esters, and amides were reported, in which an explicit new role of TosMIC as the sulfonylating agent was uncovered for the first time. Mechanistic study by control experiments and DFT calculations suggested that the reaction is initiated by Cu(OTf)2-catalyzed hydration of TosMIC to form a formamide intermediate, which undergoes facile C-S bond cleavage under the mediation of a Cs2CO3 additive.

Revisiting nucleophilic substitution reactions: Microwave-assisted synthesis of azides, thiocyanates, and sulfones in an aqueous medium

A practical, rapid, and efficient microwave (MW) promoted synthesis of various azides, thiocyanates, and sulfones is described in an aqueous medium. This general and expeditious MW-enhanced nucleophilic substitution approach uses easily accessible starting materials such as halides or tosylates in reaction with alkali azides, thiocyanates, or sulfinates in the absence of any phase-transfer catalyst, and a variety of reactive functional groups are tolerated.

N-sulfonylbenzotriazoles as advantageous reagents for C-sulfonylation

Reactions of readily available N-(alkyl-, aryl-, and heteroarylsulfonyl) benzotriazoles 3a-h with diverse nitriles, reactive heteroaromatics, alkylheteroaromatics, sulfones, and esters produced α-cyanoalkyl sulfones 5a-i, sulfonylheteroaromatics 7a-e, α-(sulfonylalkyl)heterocycles 9a-f, α-sulfonylalkyl sulfones 11a-g, and esters of α-sulfonyl acids 14a-c, respectively, in synthetically useful to excellent yields. The results represent the first examples of the successful application of sulfonylazoles for C-sulfonylation.