- Metal-free sulfonylation of arenes with: N -fluorobenzenesulfonimide via cleavage of S-N bonds: expeditious synthesis of diarylsulfones
-
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
- Feng, Yueji,Tuo, Yanyan,Zhang, Xiaohui,Zheng, Qing-Zhong
-
supporting information
p. 768 - 772
(2022/02/03)
-
- Synthesis method of diaryl sulfone compound (by machine translation)
-
The invention discloses a synthesis method of a diaryl sulfone compound, wherein the, reaction equation of the series of N - diarylsulfone compounds is prepared by (NFSI) sulfonylating the aromatic hydrocarbon under the non-metal condition with the source of the, benzenesulfonyl group as the benzenesulfonyl group, and: the reaction equation is as follows. STR3, #, STR2, #, STR2, #, #, #, # STR2. # STR2# STR2# STR2, , STR2 STR2 STR2 N - # (NFSI) STR2# STR2 STR2 STR2, #, # STR1 STR8# STR2 STR1 STR8. AlCl R3 , FeCl3 The other precious, and metals of, other metals such as the precious metals of, the other noble metals not cause the environment, to pollute, the environment and are suitable for the concise and high-efficiency synthesis of. the diarylsulfone compounds, and have good application prospects in the fields of organic synthesis, drug research and development and the like. (by machine translation)
- -
-
Paragraph 0007; 0017-0018; 0053-0055
(2019/12/31)
-
- Selective Synthesis of ortho-Substituted Diarylsulfones by Using NHC-Au Catalysts under Mild Conditions
-
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.
- Zhu, Haibo,Shen, Yajing,Wen, Daheng,Le, Zhang-Gao,Tu, Tao
-
supporting information
p. 974 - 979
(2019/02/14)
-
- A practical synthesis of aryl sulfones via cross-coupling of sulfonyl hydrazides with aryltriazenes using copper/ionic liquid combination
-
A new and efficient approach adopting copper-catalyzed cross-coupling of sulfonyl hydrazides with aryltriazenes has been developed to synthesize aryl sulfones using Br?nsted acidic ionic liquid as promoter under ambient conditions. The process employs stable and easy to handle reacting partners, and is endowed with broad substrate scope.
- Pandey, Anand Kumar,Kumar, Saurabh,Singh, Rahul,Singh, Krishna Nand
-
supporting information
p. 6704 - 6709
(2018/10/15)
-
- Synthesis of diaryl sulfones at room temperature: Cu-catalyzed cross-coupling of arylsulfonyl chlorides with arylboronic acids
-
An efficient and convenient method for the synthesis of diaryl sulfones was developed through the Cu-catalyzed cross-couplings of arylsulfonyl chlorides and arylboronic acids at room temperature in open air. This method is characterized by the use of inexpensive and readily available catalyst and substrates, mild reaction conditions, wide functionality tolerance, short reaction times for most substrates, and moderate to good yields. Stitch it up with copper: An efficient and convenient method for the synthesis of diaryl sulfones was developed through the Cu-catalyzed cross- couplings of arylsulfonyl chlorides and arylboronic acids at room temperature in open air.
- Hu, Feng,Lei, Xiangyang
-
p. 1539 - 1542
(2015/05/27)
-
- One-pot synthesis of aryl sulfones from organometallic reagents and iodonium salts
-
A transition-metal-free arylation of lithium, magnesium, and zinc sulfinates with diaryliodonium salts is described. The sulfinic acid salts were prepared from the reaction of the corresponding organometallic reagents and sulfur dioxide. Combination of the three single steps (preparation of the organometallic compound, sulfinate formation, and arylation) leads to a one-pot sequence for the synthesis of aryl sulfones from simple starting materials. The chemoselectivity of unsymmetrical diaryliodonium salts has been investigated. Potential and limitations of this method will be discussed.
- Margraf, Natalie,Manolikakes, Georg
-
p. 2582 - 2600
(2015/03/18)
-
- Metal-free, high yielding synthesis of unsymmetrical biaryl, bi(heteroaryl), aryl vinyl, aryl alkyl sulfones via coupling of aryne with sulfinic acid salts
-
Here, we report a metal-free, high yielding method for the synthesis of unsymmetrical biaryl sulfones via coupling of aryne with sulfinic acid salts. The optimized condition also works efficiently for bi(heteroaryl), aryl vinyl and aryl alkyl sulfones. The present method took comparatively shorter reaction times and has good functional group compatibility. This journal is
- Aithagani, Sravan Kumar,Yempalla, Kushalava Reddy,Munagala, Gurunadham,Vishwakarma, Ram A.,Singh, Parvinder Pal
-
p. 50208 - 50211
(2014/12/10)
-
- Metal-free synthesis of diaryl sulfones from arylsulfinic acid salts and diaryliodonium salts
-
An efficient, high-yielding, and transition-metal-free synthesis of diaryl sulfones from arylsulfinic acid salts and diaryliodonium salts has been developed. The mild reaction conditions tolerate a range of functional groups, and unsymmetrical diaryliodonium salts show high chemoselectivity.
- Umierski, Natalie,Manolikakes, Georg
-
supporting information
p. 188 - 191
(2013/03/28)
-
- Arylation of lithium sulfinates with diaryliodonium salts: A direct and versatile access to arylsulfones
-
An efficient, transition-metal-free arylation of lithium sulfinates, which are readily accessible from reactions of organolithium reagents with sulfur dioxide, is described. Based on this method, a practical protocol for the direct transformation of (hetero)arenes and (hetero)aromatic halides into diarylsulfones was developed.
- Umierski, Natalie,Manolikakes, Georg
-
p. 4972 - 4975
(2013/10/22)
-
- A Metal-Free and Microwave-Assisted Efficient Synthesis of Diaryl Sulfones
-
An efficient and general protocol for the synthesis of diaryl sulfones via the metal-free coupling of readily available diaryliodonium salts and arenesulfinates in PEG-400 under microwave irradiation has been developed. Utilizing this metal-free and eco-friendly protocol, we have prepared various diaryl sulfones in high yields and shorter reaction times under mild conditions. Furthermore, the coupling of diaryliodonium with arenesulfinate salts with and without copper iodide provides a convenient access to various diaryl sulfones with high selectivity. Georg Thieme Verlag Stuttgart · New York.
- Kumar, Dalip,Arun,Pilania, Meenakshi,Shekar, K.P. Chandra
-
p. 831 - 836
(2013/06/05)
-
- Highly selective catalytic Friedel-Crafts sulfonylation of aromatic compounds using a FeCl3-based ionic liquid
-
Friedel-Crafts sulfonylation of aromatic compounds was carried out using FeCl3-based ionic liquid. These liquids serve as efficient media as well as Lewis acid catalyst.
- Bahrami, Kiumars,Khodei, Mohammad Mehdi,Shahbazi, Fomeida
-
p. 3931 - 3934
(2008/09/21)
-
- Rapid and mild sulfonylation of aromatic compounds with sulfonic acids via mixed anhydrides using Tf2O
-
An efficient and direct sulfonylation of aromatic compounds with sulfonic acids is described via mixed anhydrides in short reaction times using Tf2O in nitromethane at room temperature.
- Alizadeh, Abdolhamid,Khodaei, Mohammd Mehdi,Nazari, Ehsan
-
p. 6805 - 6808
(2008/03/12)
-
- Direct sulfonylation of aromatic rings with aryl or alkyl sulfonic acid using supported P2O5/Al2O3
-
Direct sulfonylation of aromatic rings with aryl or alkyl sulfonic acid supported P2O5/Al2O3 (w/w 50%) under heterogeneous conditions in short reaction time and high yields. Copyright Taylor & Francis Inc.
- Hajipour, Abdol R.,Zarei, Amin,Khazdooz, Leila,Pourmousavi, Seied A.,Mirjalili, Bi Bi F.,Ruoho
-
p. 2029 - 2034
(2007/10/03)
-
- An efficient and convenient method for the synthesis of aromatic sulfones catalysed by ZrO2/S2O82- solid superacid
-
A manipulatively simple and rapid procedure for the synthesis of diaryl sulfones from arylsulfonyl chlorides with aromatic compounds is described; the reaction is conducted under Friedel-Crafts conditions in the absence of solvent using ZrO2/S2O82- as catalyst in 78-93% yields.
- Jin, Tongshou,Yang, Mina,Feng, Guoliang,Li, Tongshuang
-
p. 721 - 723
(2007/10/03)
-
- Process for the sulfonation of an aromatic compound
-
A subject-matter of the present invention is a process for the sulfonation of an activated or deactivated aromatic compound. The invention applies to the preparation of aromatic sulfones. The process for the sulfonation of an aromatic compound according t
- -
-
-
- An efficient method for aromatic Friedel-Crafts alkylation, acylation, benzoylation, and sulfonylation reactions
-
Aromatic electrophilic substitution reactions such as alkylation, acylation, benzoylation, and sulfonylation were studied in the presence of a catalytic amount of Cu(OTf)2 and Sn(OTf)2. Cu(OTf)2 was very efficient for alkylation, acylation, and benzoylation reactions. However, in case of sulfonylation reactions, Sn(OTf)2 gave better results.
- Singh, Ravi P,Kamble, Rajesh M,Chandra, Kusum L,Saravanan,Singh, Vinod K
-
p. 241 - 247
(2007/10/03)
-
- Indium-catalysed aryl and alkyl sulfonylation of aromatics
-
Commercially available indium (III) triflate is shown to be an extremely efficient catalyst for the sulfonylation of both activated and deactivated aromatics.
- Frost,Hartley,Whittle
-
p. 830 - 832
(2007/10/03)
-
- Acylation and related reactions under microwaves. 4. Sulfonylation reactions of aromatics
-
Solvent-free sulfonylation of benzene and its activated or deactivated derivatives were carried out under microwave (MW) irradiation and a catalytic amount of iron(III) chloride, which, under these conditions, is more, active than other metallic salts. With more reactive and/or nonvolatile reagents (anisole, xylenes, mesitylene) expeditious conditions (short reaction time at constant MW power without control of the temperature) were used. With less reactive and/or low-boiling reagents (benzene, toluene, halobenzenes), the rise in temperature and the increase of reaction time were controlled either by sequential MW irradiation or by a temperature order. It was shown that MWs cause preferential interactions with polar species present in the reaction, especially the aryl sulfone and its FeCl3-complexed form. A MW nonthermal effect was not observed when identical temperature gradients were produced by classical heating and MW irradiation, and if reaction temperature was strictly controlled.
- Marquie,Laporterie,Dubac,Roques,Desmurs
-
p. 421 - 425
(2007/10/03)
-
- Fe(III) exchanged montmorillonite: A mild and ecofriendly catalyst for sulfonylation of aromatics
-
Fe(III) exchanged montmorillonite clay catalyses Friedel-Crafts sulfonylation of arenes with arylsulfonyl chlorides to obtain the corresponding sulfones in excellent yields.
- Choudary,Chowdari, N. Sreenivasa,Kantam, M. Lakshmi,Kannan
-
p. 2859 - 2862
(2007/10/03)
-
- Bismuth(III) halides: Remarkable doping agents for triflic acid in the catalytic sulfonylation of arenes
-
The catalytic activity of triflic acid has been dramatically increased by the addition of a catalytic amount of bismuth(III) chloride. Thus, the catalytic sulfonylation of arenes using the new system BiCl3-triflic acid has been successfully carried out while both components of this catalytic system are poorly active or inactive alone, which suggests a synergy between BiCl3 and triflic acid. Other bismuth halide-triflic acid systems proved to be active.
- Repichet,Le Roux,Dubac
-
p. 9233 - 9234
(2007/10/03)
-