54639-46-2

Upstream product

• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 5720-05-8 4-methylphenylboronic acid 
• 106-38-7 para-bromotoluene 
• 39544-84-8 2-p-tolylsulfanylbenzothiazole 
• 2516-40-7 2-bromo-1,3-benzothiazole 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 149-30-4 2-Mercaptobenzothiazole 

Downstream Products

• 824-79-3 sodium 4-methylbenzenesulfinate 
• 54639-44-0 3-ethyl-2-[(toluene-4-sulfonyl)-triazenylidene]-2,3-dihydro-benzothiazole 
• 473935-63-6 C₁₃H₁₂Cl₆N₂O₆S 
• 70-55-3 toluene-4-sulfonamide 

Relevant academic research and scientific papers

Palladium(II)-Catalyzed Synthesis of Sulfinates from Boronic Acids and DABSO: A Redox-Neutral, Phosphine-Free Transformation

A redox-neutral palladium(II)-catalyzed conversion of aryl, heteroaryl, and alkenyl boronic acids into sulfinate intermediates, and onwards to sulfones and sulfonamides, has been realized. A simple Pd(OAc)2 catalyst, in combination with the sulfur dioxide surrogate 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO), is sufficient to achieve rapid and high-yielding conversion of the boronic acids into the corresponding sulfinates. Addition of C- or N-based electrophiles then allows conversion into sulfones and sulfonamides, respectively, in a one-pot, two-step process.

Sulfonylation of five-membered heterocycles via an SNAr reaction

An efficient, concise, and transition metal-free synthesis of functionalized sulfonylated five-membered heterocyclic compounds via an S NAr reaction has been developed. Using commercially available sodium sulfinates as sulfonylation reagents, various five-membered heterocyclic sulfones were obtained in good yields.

A mild, efficient method for the synthesis of aromatic and aliphatic sulfonamides

A two-step method was developed for the synthesis of aromatic and aliphatic sulfonamides from the corresponding sulfinates using bis(2,2,2-trichloroethyl)azodicarboxylate as the electrophilic nitrogen source. The intermediate sulfonylhydrazides were obtained in very good yields and were cleaved under reductive conditions to deliver the desired sulfonamides. A variety of substituents in the aromatic ring are well tolerated as well as heterocycles.