3753-58-0

Upstream product

• 4106-18-7 1-(phenylsulfonyl)-1H-benzo[d][1,2,3]triazole 
• 150-76-5 4-methoxy-phenol 
• 98-09-9 benzenesulfonyl chloride 
• 3313-84-6 4-nitrophenyl benzenesulfonate 
• 62790-87-8 4-(tert-butyldimethylsilyloxy)anisole 
• 133745-75-2 N-fluorobis(benzenesulfon)imide 
• 7471-26-3 N-(4-methoxyphenyl)benzenesulphonamide 
• 63082-07-5 4-methoxy-phenylcarbamate 
• 96875-66-0 N-nitroso-p-methoxy-benzenesulfonanilide 
• 65750-37-0 (2H)-p-methoxyphenol 

Downstream Products

• 54660-04-7 N-(4-methoxyphenyl)pyrrolidine 
• 84736-52-7 (+/-)-(2R,4S)-4-tert-butyl-2-(4'-methoxyphenyl)cyclohexanone 
• 53040-92-9 4-(4-tolyl)anisole 
• 874-90-8 4-methoxybenzonitrile 
• 150-76-5 4-methoxy-phenol 
• 171364-79-7 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 613-37-6 4-methoxylbiphenyl 

Relevant academic research and scientific papers

NFSI/KF mediated mild and chemoselective interconversion of aryl TBDMS ethers to their benzene sulfonate

A one pot protocol for the transformation of aryl TBDMS ethers to corresponding benzene sulfonate esters using NFSI (N-flurobenzenesulfonimide)/KF is described. In situ generation of benzenesulfonyl fluoride directs chemoselective cleavage of aryl silyl ethers over alkyl silyl ethers. Electron withdrawing substituent's on aryl ring provided better yield than donating groups. Protecting groups and sensitive functionalities are well tolerated in this methodology. Thus, commercially available inexpensive reagents, mild reaction conditions and step economy are the advantages of this method.

Deprotection of durable benzenesulfonyl protection for phenols — efficient synthesis of polyphenols

A robust protection method for phenol was demonstrated by the use of durable benzenesulfonyl group, which survives various harsh reaction conditions using Grignard reagent, organolithium reagent, metal alkoxide, phosgene, mineral, and Lewis acids. A facile deprotection condition utilizing pulverized KOH (5 equiv) and t-BuOH (10 equiv) in hot toluene makes this protocol as a practical method, which can be applied to the multistep synthesis of biologically and medicinally important polyphenol compounds.

Highly efficient Pd-catalyzed cyanation of aryl chlorides and arenesulfonates with potassium ferrocyanide in aqueous media

A highly improved Pd-catalyzed cyanation of aryl chlorides to corresponding benzonitriles was demonstrated in aqueous media. Moreover, Pd-catalyzed cyanation of aryl tosylates and benzenesulfonates with K4[Fe(CN) 6] was developed under the similar conditions, which extended application scope of the cyanation. Graphical Abstract: [Figure not available: see fulltext.]

Ether aryl sulfonic acid esters with improved antimalarial/anticancer activities

Our previous report showed that our current benchmark agent, 4-methoxyphenyl p-toluenesulibnate, is a selective antimalarial/anticancer agent. A series of related sulfones and sulfonic acid esters is now examined. 4-Allyloxyphenyl p-toluenesulfonate is a superior antimalarial/anticancer agent. 4-Methoxyphenyl 4-nitrobenzenesulfonate is a superior antimalarial agent, but shows poorer inhibition of human skin cancer cells. CSIRO 2006.

Room-Temperature Ni(0)-Catalyzed Cross-Coupling Reactions of Aryl Arenesulfonates with Arylboronic Acids

Room-temperature Ni(0)-catalyzed cross-coupling reactions of aryl arenesulfonates with arylboronic acids are described. The Ni(0) catalyst, derived from Ni(COD)2 and PCy3, proved to be a general one for the Suzuki?Miyaura cross-coupling of a variety of aryl arenesulfonates. The mild reaction condition, the readily availability of the catalyst, and excellent coupling yields make aryl arenesulfonates potentially useful substrates in organic synthesis. Copyright

Unprecedented observation of sulfonamides in the transesterification of N-unsubstituted carbamates with sulfonyl chlorides

Sulfonamides have been identified as by-products in the base-mediated transesterification of N-unsubstituted carbamates with sulfonyl chlorides to give the corresponding sulfonates. A proposed mechanism and the synthesis of hindered 2,6-disubstituted arylsulfonates via this method are also reported.

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.

1-Phenylsulfonylbenzotriazole: A novel and convenient reagent for the preparation of benzenesulfonamides and aryl benzenesulfonates

Readily available 1-phenylsulfonylbenzotriazole smoothly converts various aliphatic and aromatic amines and phenols into the corresponding benzenesulfonamides and benzenesulfonates in good yields.

Solvent Independent Transition-state Structures. Part III. Sulfonyl Transfer Reactions

A kinetic spectrophotometric study has been performed on the reactions of p-nitrophenyl benzenesulfonate (PNPBS) with m-chlorophenoxide, p-chlorophenoxide, phenoxide, p-methylphenoxide and p-methoxyphenoxide ions in DMSO-H2O mixtures at 25.0 deg C.Systema

KINETICS OF SULFONYLATION OF SUBSTITUTED PHENOLS IN THE PRESENCE OF TRIETHYLAMINE

The rate constants for the sulfonation of meta- and para-substituted phenols by benzenesulfonyl chloride in the presence of triethylamine in benzene were determined.The dependence of the rate constants on the Hammett ? constants has a V-shaped form.The effect of the leaving group was investigated, and the kinetic isotope effect was determined.The possibility of reaction by two catalytic paths (nucleophilic and general base catalysis) is discussed, and proposals were made about the reaction mechanism.