5324-75-4Relevant academic research and scientific papers
Metal-free sulfonylation of arenes with: N -fluorobenzenesulfonimide via cleavage of S-N bonds: expeditious synthesis of diarylsulfones
Feng, Yueji,Tuo, Yanyan,Zhang, Xiaohui,Zheng, Qing-Zhong
supporting information, p. 768 - 772 (2022/02/03)
A novel metal-free sulfonylation of arenes with N-fluorobenzenesulfonimide (NFSI) toward the synthesis of diarylsulfones has been developed. The reaction represents a rare example of sulfonylation reaction using NFSI as an efficient sulfonyl donor and the first example of acid-mediated sulfonylation of unactivated arenes with NFSI via selective cleavage of S-N bonds. This protocol provides a concise approach for the construction of pharmaceutically and biologically important diarylsulfones. Applications in the functionalization of natural products (e.g., β-estradiol) and in the synthesis of a key intermediate to an inhibitor of farnesyl-protein transferase, as well as in the gram-scale synthesis of the EPAC2 antagonist, are demonstrated. This journal is
Selective Synthesis of ortho-Substituted Diarylsulfones by Using NHC-Au Catalysts under Mild Conditions
Zhu, Haibo,Shen, Yajing,Wen, Daheng,Le, Zhang-Gao,Tu, Tao
supporting information, p. 974 - 979 (2019/02/14)
A single-step gold(I)-catalyzed chemoselective protocol to access ortho-substituted diarylsulfones has been established. Acenaphthoimidazolylidene gold complexes are effective catalysts for the arylsulfonylation of boronic acids by potassium metabisulfite (K2S2O5) and diaryliodonium salts to access (poly-)ortho-substituted diarylsulfones even in gram scale. Unlike the transition metal-catalyzed two-component coupling systems, the sterically hindered aryl groups in diaryliodonium salts are preferentially transferred over less bulky ones to form synthetically difficult targets, including those of pharmaceutical importance.
Organic reactions under solid-state conditions
Hajipour,Mallakpour
, p. 371 - 387 (2007/10/03)
Manipulatively simple and rapid methods are described for the synthesis of: chiral sulfinate esters from sulfonyl chlorides and sufonic acids; aldehydes and ketones from oximes, alcohols, hydrozones; sulfoxides from sulfides; and disulfides from thiols. The chemical yields are good to excellent and diastereoselectivity is high.
An efficient and novel method for the synthesis of aromatic sulfones under solvent - Free conditions
Hajipour,Mallakpour,Imanzadch
, p. 237 - 239 (2007/10/03)
A manipulative simple and rapid reaction of arensulfonyl chloride with aromatic hydrocarbons is described. The reaction is conducted under Friedel-Crafts conditions in the absences of solvent using aluminium chloride as catalysts.
Orientation in benzenesulphonylation of haloroluenes and haloanisoles - A study by NMR spectra
Gurumani, V.,Swaminathan, M.,Mangalamudaiyar, A.
, p. 281 - 287 (2007/10/02)
Halotoluenes and haloanisoles (F, Cl and Br) have been sulphonylated using benzenesulphonyl chloride and anhyd.AlCl3, and the products recovered and analysed by proton and carbon-13 NMR spectra.Formation of a minor product is found in most of the halotoluenes and in m-haloanisoles.Halogens predominantly orient the substitution in halotoluenes and methoxy group in haloanisoles.Fluorine behaves differently from other halogens in p-fluorotoluene and m-fluoroanisole.This anomaly has been discussed.Proton and carbon-13 NMR spectral data for some diphenyl sulphones obtained in benzenesulphonylation reaction have been reported.
