6324-15-8

Upstream product

• 106-41-2 4-bromo-phenol 
• 98-59-9 p-toluenesulfonyl chloride 
• 6286-84-6 2,4-dibromophenyl 4-methylbenzenesulfonate 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 104-15-4 toluene-4-sulfonic acid 

Downstream Products

• 51804-15-0 4-carboxyphenyl 4-methylbenzenesulfonate 
• 356031-48-6 4′-methoxy-[1,1′-biphenyl]-4-yl 4-methylbenzenesulfonate 
• 1208262-32-1 2',3',4',5',6'-pentafluorobiphenyl-4-yl 4-methylbenzenesulfonate 
• 1251919-77-3 4-(pyridin-2-ylmethyl)phenyl 4-methylbenzenesulfonate 
• 1262439-93-9 4-(benzylamino)phenyl 4-methylbenzenesulfonate 
• 1309660-23-8 4-(1-cyanoethyl)phenyl 4-methylbenzenesulfonate 
• 106473-33-0 4-carbamoylphenyl-4-methylbenzenesulfonate 
• 1309660-39-6 [4-(toluene-4-sulfonyloxy)phenyl]acetic acid ethyl ester 
• 1361228-70-7 ethyl 2-(4-(tosyloxy)phenyl)propanoate 
• 2050-23-9 diethyl suberate 
• 640-60-8 toluene-4-sulfonic acid phenyl ester 
• 1365610-73-6 ethyl 4-(4-(tosyloxy)phenyl)butanoate 
• 300406-05-7 4'-{[(4-methylphenyl)sulfonyl]oxy}[1,1'-biphenyl]-4-yl 4-methylbenzenesulfonate 
• 105-54-4 butanoic acid ethyl ester 

Relevant academic research and scientific papers

Electrochemical cross-coupling reactions of sodium arenesulfinates with thiophenols and phenols

A green electrochemical oxidative cross-coupling protocol for the generation of thiosulfonates and sulfonate esters using sodium arenesulfinates and thiophenols/phenols is disclosed. The protocol involves using inorganic and non-toxic NaI as both redox catalyst and supporting electrolyte at room temperature without oxidant and base. The reactions provide good yields of products and tolerate broad substrate scope. The mechanistic studies revealed that the reactions proceed via a radical pathway for the formation of SO2–S and SO2–O bonds.

Preparation method of hydroxyphenylboronic acid

The invention discloses a preparation method of hydroxyphenylboronic acid, which belongs to the technical field of boric acid synthesis in medical intermediates. The method comprises the following steps: starting from bromophenol, carrying out BOC, trimethylsilyl or benzyl protection, forming a Grignard reagent, reacting with borate, or carrying out one-pot reaction with borate and n-butyllithium,and hydrolyzing to obtain hydroxyphenylboronic acid. According to the invention, cheap and easily available protecting groups are adopted, so that the protecting groups are easy to remove during boronation reaction hydrolysis, industrial amplification is easy to realize, batch production is carried out on the scale of dozens of kilograms, and the process stability is good.

Design, synthesis and comparative analysis of triphenyl-1,2,3-triazoles as anti-proliferative agents

Herein, a series of triaryl-1,2,3-triazoles, in order to check cytotoxicity on breast cancer cell lines have been synthesized with pendent benzyl ring to mimic the phenolic A ring of Tamoxifene. The biological results indicated that most of the compounds

Effect of charged and ortho substituents on 17O NMR chemical shifts of substituted phenyl tosylates in DMSO

The 17O nuclear magnetic resonance chemical shifts for 31 ortho-substituted, para-substituted, and meta-substituted phenyl esters of 4-methylbenzenesulfonic acid (phenyl tosylates, 4-CH3-C6H4SO2OC6H4-X) with the neutral and charged substituents in phenoxy part were measured in DMSO-d6 at 50°C. The chemical shifts, δ(17O), of the sulfonyl (SO2) and single-bonded phenoxy (O─Ph) oxygens for para and meta derivatives in the case of neutral substituents showed a good correlation with the Taft σI and σ°R substituent constants. The influence of the ortho substituents on the δ(17O) chemical shifts of the sulfonyl oxygens and single-bonded phenoxy oxygens was found to be described well with the Charton equation: δ(17O)ortho?=?δ(17O)H?+?ρI σI?+?ρRσ°R?+?δEBs when the data treatment was performed separately for electron-donating +R substituents and electron-withdrawing ?R substituents. The substituent constants, σ°X±, for the charged substituents (4-N+(CH3)3I?, 3-N+(CH3)3I?, 2-N+(CH3)3I?, 4-COO?N+Bu4, 3-COO?N+Bu4, 2-COO?N+Bu4) calculated from the δ(17O) chemical shifts for phenyl tosylates in DMSO prove that in DMSO, the compounds involving charged substituents are predominantly in ion pair form and not dissociated into free ions. The same conclusion was drawn recently from the carbonyl IR stretching frequencies, νCO, and the carbonyl carbon 13C chemical shifts for substituted phenyl benzoates, C6H5CO2C6H4-X, in DMSO. It was shown that for ion pairs of the charged substituents in DMSO and concentrated aqueous salt solution, the same substituent constant, σ°X±, could be used.

Copper-Catalyzed Regioselective C-H Sulfonyloxylation of Electron-Rich Arenes with p-Toluenesulfonic Acid and Sulfonyloxylation of Aryl(mesityl)iodonium Sulfonates

Copper-catalyzed regioselective C-H sulfonyloxylation of electron-rich arenes with p-toluenesulfonic acid has been developed. Electron-rich benzene derivatives and heteroarenes can undergo this C-H sulfonyloxylation reaction to generate aryl tosylates. Furthermore, sulfonyloxylation of aryl(mesityl)iodonium sulfonates has also been investigated. Both aryl(mesityl)iodonium tosylates and triflates can react smoothly to get aryl sulfonates. The formed aryl sulfonates can be converted to phenols, as well as used as good partners of cross-coupling reactions.

DBN hexafluorophosphate salts as convenient sulfonylating and phosphonylating agents

Air-stable N-sulfonyl and N-phosphonyl DBN hexafluorophosphate salts have been synthesised under mild conditions as sulfonylating and phosphonylating agents. These salts are highly efficient in the sulfonylation and phosphonylation of a range of N- and O-nucleophiles to generate sulfonamides, sulfonate esters, phosphoramidates and phosphonate esters in good yields.

Iodine-induced synthesis of sulfonate esters from sodium sulfinates and phenols under mild conditions

An iodine-induced synthesis of sulfonate esters via cross-coupling reactions of sodium sulfinates with phenols is reported. This synthetic route is low-cost, facile, green and efficient, and could afford the target products with good to excellent yields u

Ti/Ni-mediated inter- and intramolecular conjugate addition of aryl and alkenyl halides and triflates

In this work, we show that the unique combination of a nickel catalyst and Cp2TiCl allows the direct conjugate addition of aryl and alkenyl iodides, bromides, and to a lesser extent, chlorides and triflates to α,β-unsaturated carbonyls at room temperature, without requiring the previous formation of an organometallic nucleophile. The reaction proceeds inter- and intramolecularly with good functional group compatibility, which is key for the development of free protecting group methodologies. Carbo- and heterocycles of five- and six-membered rings are obtained in good yields. Moreover, some insights about the mechanism involved have been obtained from cyclic voltammetry, UV-vis, and HRTEM measurements.

Cs2CO3 catalyzed rapid and efficient conversion of amines into sulfonamides; Alcohols and phenols into sulfonic esters

A simple and efficient method has been developed for the sulfonylation of several amines, alcohols, and phenols by p-toluenesulphonylchloride (p-TsCl) in the presence of catalytic amount of Cs2CO3 at 25C to obtain sulfonamides and sulfonic esters in very good yields. Cs2CO3 has been found to be highly efficient catalyst. Taylor & Francis Group, LLC.

Preparation of polyfunctional arylmagnesium, arylzinc, and benzylic zinc reagents by using magnesium in the presence of LiCl

The presence of LiCl considerably facilitates the insertion of magnesium into various aromatic and heterocyclic bromides. Several functional groups, such as -OBoc, -OTs, -Cl, -F, -CF3, -OMe, -NMe2, and -N 2NR2, are well tolerated. The presence of a cyano group leads in some cases to competitive reduction of the organic halide to the corresponding ArH compound. The presence of sensitive groups such as methyl or ethyl ester is tolerated upon in situ trapping of the intermediate magnesium reagent with ZnCl2. This method can also be applied to the preparation of functionalized benzylic zinc reagents from benzylic chlorides. In the case of di- or tribromoaryl derivatives, directing groups such as -OPiv, -OTs, -N2NR2, or -OAc orient the zinc insertion (Zn/LiCl) to the ortho-position, while the reaction with Mg/LiCl or Mg/LiCl/ZnCl 2 leads to regioselective insertion into the para-carbon-bromine bond. Large-scale experiments (20-100 mmol) for all of the metalation procedures are described.