- Isocyanide-Induced Esterification of Sulfinic Acids to Access Sulfinates
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The isocyanide-induced esterification of sulfinic acids with alcohols or thiophenols access to sulfinates has been developed. Various primary, secondary, and tertiary alcohols could be compatible with the established protocols. Notably, such an isocyanide-induced synthetic strategy presented the advantages of simple operation, good functional group tolerance, and more than 40 examples up to 99% yields. (Figure presented.).
- Yang, Jianjing,Dong, Haozhe,Yan, Kelu,Song, Xiaodan,Yu, Jie,Wen, Jiangwei
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supporting information
p. 5417 - 5421
(2021/09/29)
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- NaHSO3-Mediated Direct Synthesis of Sulfinic Esters from Sulfonyl Hydrazides under Transition-Metal-Free Conditions
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We have developed a protocol for the NaHSO3-promoted esterification of sulfonyl hydrazides with alcohols for the synthesis of sulfinic esters. Various sulfonyl hydrazides could be converted to the corresponding sulfinic esters in good to high yields. The merits of this protocol include mild transition-metal-free reaction conditions, an inexpensive and available reagent, and operational simplicity. Controlled experiments reveal that this transformation probably undergoes via a radical pathway. (Figure presented.).
- Zhang, Guofu,Fan, Qiankun,Wang, Huimin,Zhao, Yiyong,Ding, Chengrong
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p. 833 - 837
(2020/12/07)
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- Direct synthesis of sulfinic esters via ultrasound accelerated tandem reaction of thiols and alcohols with N-bromosuccinimide
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The direct transformation of various thiols and simple alcohols with N-bromosuccinimide into sulfinic esters has been investigated by using different categories of base/acidic catalysts as well as co-solvents under varied reaction conditions. The reaction was found out to afford the sulfinic esters with high yields in the absence of catalysts, especially within the shorter time under the acceleration of ultrasonic irradiation than under the longer-lasting conventional stirring conditions.
- Nguyen, Lan-Anh Thi,Le, Tri-Nghia,Duong, Cong-Thang,Vo, Chi-Tam,Duus, Fritz,Luu, Thi Xuan Thi
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p. 519 - 528
(2021/05/27)
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- Electrochemical Synthesis of Sulfinic Esters via Aerobic Oxidative Esterification of Thiophenols with Alcohols
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A method for the electrochemical synthesis of sulfinic esters by aerobic oxidative coupling of thiophenols and alcohols has been developed. Using electrons as the redox reagent and O 2in air as the oxygen source, the reactions proceeded smoothly at room temperature, even for a gram-scale preparation. No use of catalyst, clean redox reagent, green and abundant oxygen source, and mild reaction conditions make this strategy eco-friendl.
- Zhou, Hongyan,Duan, Jiaokui,Xie, Dongtai,Yang, Jingya,Ma, Ben,Wang, Ganggang,Wu, Chengqi,Wang, Xi-Cun
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p. 2705 - 2712
(2020/09/15)
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- Efficient electrosynthesis of sulfinic esters via oxidative cross-coupling between alcohols and thiophenols
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A new protocol for S O bond formation was developed by electrochemical oxidative cross-coupling between alcohols and thiophenols. With this strategy, a series of valuable sulfinic ester derivatives were synthesized up to 96% yield from basic starting materials. A preliminary mechanistic investigation reveals that this reaction involves oxygen reduction reaction (ORR).
- Gong, Fengping,Lu, Fangling,Zuo, Lin,Wang, Qi,Li, Ru,Hu, Jiaxin,Li, Zhen,Takfaoui, Abdelilah,Lei, Aiwen
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p. 192 - 196
(2019/09/13)
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- Ni/NHC-catalyzed cross-coupling of methyl sulfinates and amines for direct access to sulfinamides
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It was reported to develop a simple and convenient method for the Ni/NHC-catalyzed cross-coupling of methyl sulfinates and amines without an acid/base to afford secondary or tertiary sulfinamides in moderate to good yields. The method can provide the desired products with broad substrate scope, good chemoselectivity and good functional group compatibility. The presented approach may enrich the Ni/NHC catalyst system and promote the applications of methyl sulfinates in the organic sulfur chemistry.
- Li, Gang-Jian,Pan, You-Lu,Liu, Yan-Ling,Xu, Hai-Feng,Chen, Jian-Zhong
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supporting information
(2019/10/28)
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- A aryl sulfonic acid ester compound synthesis method (by machine translation)
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The invention relates to medicine, in the field of organic chemical and fine chemical industry, and in particular relates to a simple, highly efficient method for preparing aryl sulfonic acid ester compound. The method is to four fluoro boric acid aryl diazonium salt, double-(sulfur dioxide) - 1, 4 - diazabicyclo [2.2.2] octane adduct (DABSO) and alcohol as the raw material, the copper salt catalyst, under the presence of an oxidant, nitrogen protection, 50 - 100 °C heating under the reaction conditions, it took 10 - 15 hours synthetic aryl sulfonate. The reaction through simple after treatment can be a high yield a series of aryl sulfonic acid ester compound. On the benzene ring with various substituted aryl four fluoroborates, ordinary primary alcohol, secondary alcohol can be utilized as a reaction substrate, to obtain the corresponding asia sulfonic acid ester. (by machine translation)
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Paragraph 0024; 0042; 0043
(2019/06/12)
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- Metal- And oxidant-free electrochemical synthesis of sulfinic esters from thiols and alcohols
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An efficient and eco-friendly electrochemical synthesis of various sulfinic esters from thiols and alcohols via sequential S-H/S bond cleavage and double S-O bond formation under mild reaction conditions has been developed. Stoichiometric oxidants, metal catalysts, activating agents and even added bases were avoided in this method, and the only by-product generated from this reaction was dihydrogen gas which could serve as a green source of energy. Various functional groups are compatible with this green protocol which can be easily conducted on a gram-scale.
- Ai, Chongren,Shen, Haiwei,Song, Dingguo,Li, Yujin,Yi, Xiao,Wang, Ze,Ling, Fei,Zhong, Weihui
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supporting information
p. 5528 - 5531
(2019/10/22)
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- A sustainable oxidative esterification of thiols with alcohols by a cobalt nanocatalyst supported on doped carbon
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Here, we developed a new cobalt nanocatalyst supported on N-SiO2-doped activated carbon (Co/N-SiO2-AC), which exhibits excellent catalytic performance towards the oxidative esterification of (hetero)aryl and alkyl thiols with alcohols. A wide array of sulfinic esters were efficiently afforded in an exclusive chemoselective manner. The developed synthetic method proceeds with the merits of mild reaction conditions, broad substrate scope, operational simplicity, good functional group tolerance, earth-abundant and reusable cobalt catalysts, the utilization of renewable alcohols as the coupling partners and molecular O2 as the sole oxidant, which offers a practical method for sustainable synthesis of sulfinic esters.
- Zhou, Changjian,Tan, Zhenda,Jiang, Huanfeng,Zhang, Min
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supporting information
p. 1992 - 1997
(2018/05/23)
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- Facile aerobic photo-oxidative synthesis of sulfinic esters
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A mild and efficient one-pot visible light-induced method has been developed for the synthesis of sulfinic esters. Sulfinic esters are important structural elements that are frequently found in pharmaceutical agents and biologically active natural products. The routine procedure in the drug discovery and development process to prepare and fully characterize sulfinic esters make them a drug candidate for biological evaluation.
- Singh, Pravin K.,Singh, Praveen P.,Srivastava, Vishal
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p. 383 - 387
(2019/03/14)
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- Copper-Catalyzed Aerobic Oxidative Reaction of Sulfonyl Hydrazides with Alcohols: An Easy Access to Sulfinates
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A Cu-catalyzed aerobic oxidative reaction between sulfonyl hydrazides and alcohols has been developed. In this reaction, sulfonyl hydrazides act as the sulfinic acid precursors to react with alcohols, resulting in sulfinic esters with up to 72 % yield. This catalytic system tolerates a wide range of sulfonyl hydrazide substrates, and represents a new strategy for the transformation of readily available sulfonyl hydrazides.
- Du, Bingnan,Li, Zan,Qian, Ping,Han, Jianlin,Pan, Yi
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p. 478 - 481
(2016/03/08)
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- COMPOSITION, SYNTHESIS, AND USE OF NEW ARYLSULFONYL ISONITRILES
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This invention relates to novel isonitriles, including arylsulfonyl isonitriles, and methods for their synthesis. The isonitriles include a conjugated ring system. The structure is designed with the flexibility to have multiple substitution patterns. The isonitriles may be used in applications including, but not limited to, pharmaceutical compositions.
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Paragraph 0145
(2015/09/23)
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- Alkyl sulfinates: Formal nucleophiles for synthesizing TosMIC analogs
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Alkyl sulfinates function as formal nucleophiles in Mannich-type reactions to give sulfonyl formamides, which are readily dehydrated to the corresponding sulfonylmethyl isonitriles. The efficient, two-step synthesis provides a general route to sulfonylmethyl isonitriles from readily available methyl sulfinates or thiols. Mechanistic analysis reveals that the unusual nucleophlicity of the alkyl sulfinates arises from the in situ release of sulfinic acids.
- Lujan-Montelongo, J. Armando,Estevez, Angel Ojeda,Fleming, Fraser F.
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supporting information
p. 1602 - 1605
(2015/03/04)
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- Catalytic oxidation of alcohols and sulfides with hydrogen peroxide using isoindoline and phthalazine-based diiron complexes
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A series of diiron(III) complexes of 1,3-bis(2′-arylimino) isoindoline, [(Fe(L)Cl)2O] and 1,4-di-(2′-aryl) aminophthalazine, [Fe2(μ-OMe)2(H2L)Cl 4], including new structurally characterized ligands, 1,4-di-(4′-methyl-2′-thiazolyl)aminophthalazine and 1,4-di-(2′-benzthiazolyl)-aminophthalazine, have been characterized, and used as catalysts for the oxidation of para-substituted phenyl methyl sulfides and benzyl alcohols. Hammett correlations and kinetic isotope effect experiments support the involvement of electrophilic metal-based oxidants. In case of [(Fe(L1,2)Cl)2O] catalysts, direct correlation has been found between the oxidative and catalase-like activity.
- Szávuly, Miklós,Szilvási, Szilvió D.,Csonka, Róbert,Klesitz, Dániel,Speier, Gábor,Giorgi, Michel,Kaizer, József
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p. 317 - 324
(2014/08/05)
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- The synthesis of sulfinylphthalimides and their reactions with some nucleophiles in dioxane
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In this study, some N-(p-substituted-arylsulfinyl)phthalimides (1a-1e) were synthesized. The synthesized compounds were examined with respect to their substitution reactions with sodium ethoxide, sodium methoxide, methylamine, and t-butylamine in dioxane.
- Bozkurt, Yasemin Soydas,Kutuk, Halil
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experimental part
p. 2250 - 2257
(2012/03/27)
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- Methyl sulfinates as electrophiles in friedel-crafts reactions. Synthesis of aryl sulfoxides
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The Friedel-Crafts reaction of methyl alkyl- and arylsulfinates with aromatic systems, activated by one or more electron-donating substituents (OH, OMe, NHR, NR2), provides alkyl aryl and diaryl sulfoxides under mild conditions and in moderate to good yields. The very high regioselectivity usually observed in these sulfinylation reactions is rationalized on the basis of a Wheland intermediate having a trigonal bypyramidal structure in which steric and electronic interactions are significant factors strongly destabilizing the attack to the ortho positions.
- Yuste, Francisco,Hernandez Linares, Angelica,Mastranzo, Virginia M.,Ortiz, Benjamin,Sanchez-Obregon, Ruben,Fraile, Alberto,Garcia Ruano, Jose Luis
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p. 4635 - 4644
(2011/07/29)
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- Hypervalent iodine in synthesis. XXIV: A facile method for the preparation of arylsulfinic esters: Oxidation of disulfides or thiophenols by phenyliodine(III) bis(trifluoroacetate) in the presence of alcohols
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Arylsulfinic esters were prepared by the oxidation of diaryl disulfides or thiophenols with phenyliodine(III) bis(trifluoroacetate) in the presence of alcohols.
- Xia,Chen
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p. 1321 - 1326
(2007/10/03)
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- NMR of Terminal Oxygen, 6 - 17O NMR of the S-O 'Double Bond': Derivatives of Arylsulphinic and Arylsulphonic Acids
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The 17O NMR spectra of terminal oxygen atoms in esters, anions and amides of substituted arenesulphinic acids and in esters and amides of substituted arenesulphonic acids were measured.The signals of the terminal O appear close to those of the bridge O.Co
- Dahn, Hans,Toan, Vien Van,Ung-Truong, My-Ngoc
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p. 897 - 903
(2007/10/02)
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