- Synergistic Dual Role of [hmim]Br-ArSO2Cl in Cascade Sulfenylation-Halogenation of Indole: Mechanistic Insight into Regioselective C-S and C-S/C-X (X = Cl and Br) Bond Formation in One Pot
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Bifunctionalized indoles are an important class of biologically active heterocyclic compounds and potential drug candidates. Because of the lack of efficient synthetic methods, one pot cascade synthesis of these compounds is rare and remains a challenge.
- Equbal, Danish,Singh, Richa,Saima,Lavekar, Aditya G.,Sinha, Arun K.
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supporting information
p. 2660 - 2675
(2019/03/14)
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- N-bromosuccinimide mediated decarboxylative sulfonylation of β-keto acids with sodium sulfinates toward β-keto sulfones: Evaluation of human carboxylesterase 1 activity
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A N-bromosuccinimide (NBS) mediated decarboxylative sulfonylation of β-keto acids with sodium sulfinates is developed. The transformation exhibits a broad substrate scope and good functional group tolerance. Preliminary mechanistic studies showed that this reaction is likely to proceed through a nucleophilic substitution of β-keto acid with sulfonyl bromide pathway. All synthesized β-keto sulfones were evaluated the inhibitory effect against human carboxylesterase 1 (CES1). This investigation offers an expedient strategy for efficient synthesis of β-keto sulfones that are widely present in biologically active natural products and pharmaceutical agents.
- Han, Fuzhong,Su, Bobo,Song, Peifang,Wang, Yaqiao,Jia, Lina,Xun, Shanshan,Hu, Minggang,Zou, Liwei
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p. 5908 - 5913
(2018/08/29)
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- Sulfonyl halide synthesis by thiol oxyhalogenation using NBS/NCS – iPrOH
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A rapid and facile method provides a general route to sulfonyl bromides/chlorides by the oxidation of thiols using NXS – ROH (X?=?Br,Cl, R?=?iPr) as an oxyhalogenation reagent. Control experiments suggest that the alcohol component is the source of oxygen. The proposed method enable the access to structurally diverse sulfonyl bromides and chlorides including challenging examples, inaccessible by other synthetic methods.
- Silva-Cuevas, Carolina,Perez-Arrieta, Carlos,Polindara-García, Luis A.,Lujan-Montelongo, J. Armando
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supporting information
p. 2244 - 2247
(2017/05/16)
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- Conversion of thiols into sulfonyl halogenides under aerobic and metal-free conditions
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An environmentally benign, metal-free synthesis of sulfonyl chlorides and bromides from thiols in the presence of ammonium nitrate, an aqueous solution of HCl and HBr and oxygen as a terminal oxidant was developed. The reactivity of various substituted thiophenols, benzylic-, aliphatic- and heteroaromatic thiols was examined. Ammonium nitrate served as a source of nitrogen oxides (NO/NO2), which are the crucial players in a redox-catalytic cycle. Sulfonyl chlorides and bromides were isolated without extraction and "filtered" over a short pad of silica gel; the use of solvents was greatly reduced in comparison with traditional isolation and purification. A "one-pot" protocol for the conversion of thiol into sulfonamide is also demonstrated. Scale-up experiments on the preparation of sulfonyl chloride and bromide are shown. A possible reaction pathway is discussed.
- Jereb, Marjan,Hribernik, Luka
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supporting information
p. 2286 - 2295
(2017/07/24)
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- METHOD FOR PRODUCING SULFONYL BROMIDE COMPOUNDS
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PROBLEM TO BE SOLVED: To provide a method capable of producing sulfonyl bromide compounds which are useful as an intermediate such as a medicine, an agrochemical and a functional materials safely, simply and in a high yield. SOLUTION: There is provided a
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Paragraph 0032
(2017/04/27)
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- Direct difunctionalization of alkenes with sulfinic acids and NBS leading to β-bromo sulfones
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A new and metal-free method has been developed for the synthesis of β-bromo sulfones through the direct difunctionalization of alkenes with sulfinic acids and NBS. This protocol provides a simple, convenient, and efficient approach to various β-bromo sulf
- Wei, Wei,Liu, Xiaoxia,Yang, Daoshan,Dong, Ruimei,Cui, Ying,Yuan, Fei,Wang, Hua
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supporting information
p. 1808 - 1811
(2015/03/30)
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- Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/bromides using oxone-KX (X = Cl or Br) in water
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A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides by oxyhalogenation of thiols and disulfides with oxone-KX (X = Cl or Br) using water as the solvent is described. This journal is the Partner Organisations 2014.
- Madabhushi, Sridhar,Jillella, Raveendra,Sriramoju, Vinodkumar,Singh, Rajpal
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supporting information
p. 3125 - 3131
(2014/06/10)
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- METHOD FOR PRODUCING SULFONIC ACID HALIDE COMPOUND
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PROBLEM TO BE SOLVED: To provide a method for producing a sulfonic acid halide compound without using chlorine gas requiring careful handling. SOLUTION: This method for producing the sulfonic acid halide compound represented by formula (3) (Ar is an aroma
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Page/Page column 7
(2008/06/13)
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- Unexpected differences in the α-halogenation and related reactivity of sulfones with perhaloalkanes in KOH-t-BuOH
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Most alkyl phenyl sulfones are readily α-chlorinated with CCl4 and α-brominated with CBrCl3 in KOH-t-BuOH via radical-anion radical pair (RARP) reactions. While isopropyl mesityl sulfone (4) is easily α-chlorinated with CCl4, it was completely recovered when treated with the more reactive CBrCl3. Subsequent investigations showed the latter result to be due to the poor acidity of 4 together with the rapid depletion of CBrCl3 and KOH by their reaction with each other, and led to a variety of other important results. 4-Hydroxyphenyl isopropyl sulfone (6) is unreactive with either CCl4 or CBrCl3 in KOH-t-BuOH, its phenoxide anion strongly reducing the electronegativity of the sulfonyl group, thereby inhibiting α-anion formation. This effect is reversed by the electron-withdrawing influence of two α-phenyls, so that benzhydryl 4-hydroxyphenyl sulfone (8) is readily α-halogenated in KOH-t-BuOH with CCl4 or CBrCl3. On further contact with KOH-t-BuOH the α-halogenated sulfones from 8 are decomposed into benzophenone and phenol. While the α-halogenated derivatives of 4-methoxyphenyl benzhydryl sulfone (9) are stable to base, they are decomposed even under mildly acidic conditions into 4-methoxyphenyl 4-methoxybenzenethiolsulfonate (9c), phenol, and benzophenone. Mono-α-halogenation of benzyl phenyl sulfone (10) enhances the rate of the subsequent halogenation, so that α,α-dihalogenation is attained while much substrate is still present and the mono-α-halogenated product is not detected. The ease of reductive debromination of α-bromo sulfones with Cl3C- was correlated with the stability of the formed α-anions, explaining the success with α-bromobenzylic sulfones but failure with α-bromoalkyl sulfones. In the presence of air and the absence of competing halogenation, formation of the α-anions of alkyl aryl sulfones is quickly accompanied by oxidative cleavage by atmospheric O2, leading to the formation of arenesulfonyl alcohols, arenesulfonyl halides, and haloarenes.
- Meyers, Cal Y.,Chan-Yu-King, Roch,Hua, Duy H.,Kolb, Vera M.,Matthews, Walter S.,Parady, Thomas E.,Horii, Toyokazu,Sandrock, Paul B.,Hou, Yuqing,Xie, Songwen
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p. 500 - 511
(2007/10/03)
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- Preparation of sulfonamides from sodium sulfonates: Ph3P·Br2 and Ph3P·Cl2 as a mild halogenating reagent for sulfonyl bromides and sulfonyl chlorides
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Arene- and alkanesulfonamides were prepared by treatment of the corresponding sodium sulfonates with triphenylphosphine dibromide or dichloride followed by amines in the presence of triethylamine via sulfonyl halides. Reactions of sodium aminosulfonates gave cyclized products. Amidation of p-toluenesulfonic acid with triphenylphosphine dichloride was also examined to give N-benzyl-p-toluenesulfonamide. Methyl p- toluenesulfonate was obtained by esterification of sodium p-toluenesulfonate via p-toluenesulfonyl chloride.
- Kataoka, Tadashi,Iwama, Tetsuo,Setta, Tomofumi,Takagi, Atsuko
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p. 423 - 426
(2007/10/03)
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- Synthesis and Properties of 1-Substituted-2-(phenylsulfonyl)-3-phenyl-2-propenes
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The regiospecific photolytic addition of benzenesulfonyl bromide to 1-phenylpropene served as a key step in the synthesis of 2-(phenylsulfonyl)-1-phenyl-1-propene (1a).The propenyl substrate 1a was brominated with N-bromosuccinimide in refluxing carbon te
- Doomes, Earl,Clarke, Ursula,Neitzel, James J.
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p. 1540 - 1543
(2007/10/02)
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- SULFENYL CHLORIDES, XIV; THE REACTION OF ARYLTHIOSULFONATES WITH ARYLSULFENYL HALIDES
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Utilizing partial results published earlier , the sulfenylation reaction of aromatic thiolsulfonates was investigated.Aromatic thiolsulfonates rapidly react with sulfenyl bromide in acetonitrile solution, whereas with sulfenyl chloride the splitting of the thiolsulfonate bond proceeds only in dimethylformamide and under forceful conditions.
- Lazar, J.,Vinkler, E.
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p. 171 - 174
(2007/10/02)
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