13656-61-6

Upstream product

• 349-88-2 4-Fluorobenzenesulfonyl chloride 
• 108-95-2 phenol 
• 405-31-2 bis(4-fluorophenyl)disulfide 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 1529-17-5 phenyltrimethylsilyl ether 
• 368-85-4 4-fluorobenzenesulfonyl fluoride 
• 824-80-6 sodium 4-fluorobenzenesulfinate 
• 349-89-3 p-chlorobenzenesulfonyl fluoride 

Downstream Products

• 93-89-0 benzoic acid ethyl ester 
• 3007-71-4 N-octylaniline 
• 92-52-4 biphenyl 

Relevant academic research and scientific papers

Practical Electro-Oxidative Sulfonylation of Phenols with Sodium Arenesulfinates Generating Arylsulfonate Esters

A practical and sustainable synthesis of arylsulfonate esters has been developed through electro-oxidation. This reaction employed the stable and readily available phenols and sodium arenesulfinates as the starting materials and took place under mild reaction conditions without additional oxidants. A wide range of arylsulfonate esters including those bearing functional groups were produced in good to excellent yields. This reaction could also be conducted at a gram scale without a decrease of reaction efficiency. Those results well demonstrated the potential synthetic value of this reaction in organic synthesis.

One-pot fluorosulfurylation of Grignard reagents using sulfuryl fluoride

Herein, we report a new method for the one-pot syntheses of sulfonyl fluorides. Addition of an alkyl, aryl, or heteroaryl Grignard to a solution of sulfuryl fluoride at ambient temperature affords the desired sulfonyl fluorides in 18-78% yield. Furthermore, this method is applicable for in situ sequential reactions, whereby the Grignard reagent can be converted to the corresponding diarylsulfone, sulfonate ester, or sulfonamide in a one-pot process.

One-pot tandem reactions for direct conversion of thiols and disulfides to sulfonic esters, and Paal-Knorr synthesis of pyrrole derivatives catalyzed by TCCA

A convenient synthesis of sulfonic esters from thiols and disulfides is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with trichloroisocyanuric acid (TCCA), tetra-butylammonium chloride (t-Bu4NCl), and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of N-substituted pyrroles by the reaction of hexane-2,5-dione with primary amines has been accomplished using TCCA as a catalyst under mild condition with excellent yields.

One-pot tandem reactions for direct conversion of thiols and disulfides to sulfonic esters, alcohols to bis(indolyl)methanes and synthesis of pyrroles catalyzed by N-chloro reagents

A convenient synthesis of sulfonic esters from thiols and disulfides has been described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with Chloramin-T, tetra-butylammonium chloride (t-Bu4NCl) and water. The sulfonyl chlorides are then further allowed to react with phenol derivatives in the same reaction vessel. Also, a facile synthesis of bis(indolyl)methanes from alcohols using TCCA/KBr/wet-SiO2, and N-substituted pyrroles by reaction of hexane-2,5-dione with primary amines has been accomplished under mild condition with excellent yields.

Synthesis of sulfonamides and sulfonic esters via reaction of amines and phenols with thiols using H2O2-POCl3 system

Phosphorus oxychloride efficiently promoted the synthesis of sulfonamides and sulfonic esters from thiols with hydrogen peroxide in the presence of Amberlite IRA-400 (OH-). This method has been applied to a variety of substrates including nucleophilic and sterically hindered amines, and also phenols with excellent yields of sulfonamides and sulfonic esters. In most cases these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity.

Palladium-catalyzed amination of aryl and heteroaryl tosylates at room temperature

Mild palladium-catalyzed aminations of aryl tosylates and the first aminations of heteroaryl tosylates are described. In the presence of the combination of L2Pd(0) (L = P(o-tol)3) and the hindered Josiphos ligand CyPF-t-Bu, a variety of primary alkylamines and arylamines react with both aryl and heteroaryl tosylates at room temperature to form the corresponding secondary arylamines in high yields with complete selectivity for the monoarylamine. These reactions at room temperature occur in many cases with catalyst loadings of 0.1 mol % and 0.01 mol % in one case, constituting the most efficient aminations of aryl tosylates by nearly 2 orders of magnitude. This catalyst is made practical by the development of a convenient method to synthesize the L2Pd(0) precursor. This complex is stable to air as a solid. In contrast to conventional relative rates for reactions of aryl sulfonates, the reactions of aryl tosylates are faster than parallel reactions of aryl triflates, and the reactions of aryl tosylates are faster than parallel or competitive reactions of aryl chlorides. Copyright

An efficient catalyst for PD-catalyzed carbonylation of aryl arenesulfonates

(Chemical Equation Presented) Aryl carboxylic esters were synthesized by Pd-catalyzed carbonylation of aryl p-fluorobenzenesulfonates or -tosylates. A unique Josiphos ligand was discovered through high-throughput catalyst screening, which was the key for the successful carbonylation of various substrates. This catalyst is effective and works well for both electron-rich and electron-poor aryl arenesulfonates. Isolated yields of up to 90% were obtained for aryl p-fluorobenzenesulfonates and -tosylates.

Aryl Mesylates in Metal-Catalyzed Homocoupling and Cross-Coupling Reactions. 1. Functional Symmetrical Biaryls from Phenols via Nickel-Catalyzed Homocoupling of Their Mesylates

Aryl sulfonates including mesylate derived from phenols are converted in high yields to biaryls by homocoupling in the presence of catalytic amounts of zero-valent nickel catalysts generated in situ.This reaction provides the most convenient method for the synthesis of many functional symmetrical biaryls and was applied to the preparation of 2,2'-, 3,3'-, and 4,4'-disubstituted biphenyls and other biaryls.The influence of the electronic and steric effects of substituents attached in the ortho, meta, and para positions of aryl sulfonates and the nature of the sulfonate leaving group on the yield of homocoupled product as well as their influence on the extent of various side reactions were investigated.In addition, the influence of the effects of the polarity and dryness of solvent, halide ion source and concentration, and ratio of catalyst and ligand to aryl sulfonate are discussed.