23730-24-7Relevant articles and documents
Isocyanide-Induced Esterification of Sulfinic Acids to Access Sulfinates
Yang, Jianjing,Dong, Haozhe,Yan, Kelu,Song, Xiaodan,Yu, Jie,Wen, Jiangwei
supporting information, p. 5417 - 5421 (2021/09/29)
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.).
Efficient electrosynthesis of sulfinic esters via oxidative cross-coupling between alcohols and thiophenols
Gong, Fengping,Lu, Fangling,Zuo, Lin,Wang, Qi,Li, Ru,Hu, Jiaxin,Li, Zhen,Takfaoui, Abdelilah,Lei, Aiwen
, p. 192 - 196 (2019/09/13)
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).
Electrochemical Synthesis of Sulfinic Esters via Aerobic Oxidative Esterification of Thiophenols with Alcohols
Zhou, Hongyan,Duan, Jiaokui,Xie, Dongtai,Yang, Jingya,Ma, Ben,Wang, Ganggang,Wu, Chengqi,Wang, Xi-Cun
, p. 2705 - 2712 (2020/09/15)
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.
A aryl sulfonic acid ester compound synthesis method (by machine translation)
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Paragraph 0024; 0036; 0037, (2019/06/12)
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)
Sodium Arenesulfinates-Involved Sulfinate Synthesis Revisited: Improved Synthesis and Revised Reaction Mechanism
Ji, Yuan-Zhao,Li, Hui-Jing,Zhang, Jin-Yu,Wu, Yan-Chao
, p. 1846 - 1855 (2019/02/14)
Reaction of alcohols with sodium arenesulfinates could afford either sulfones or sulfinates, and O-attack of sulfinate anions onto the in situ generated carbocation intermediates from alcohols was the previous proposed reaction mechanism in many syntheses of sulfinates. This concept, which is often used consciously or unconsciously, was revised herein by using isotopic labeling experiments and development of an improved sulfinate synthesis. The improved sulfinate synthetic protocol possesses many advantages such as a high sulfinate/sulfone selectivity, a broad substrate scope, metal-free, and mild reaction conditions. The revised reaction mechanism necessitates revision of many previous proposed reaction mechanisms in literatures.
Substrate- and temperature-controlled divergence in reactions of alcohols with TosMIC catalyzed by BF3 · Et2O: Facile access to sulfinates and sulfones
Pogaku, Naresh,Krishna, Palakodety Radha,Prapurna, Y. Lakshmi
supporting information, p. 1239 - 1249 (2017/07/06)
An efficient BF3 · Et2O-catalyzed divergent synthesis of sulfinate esters and sulfones through C–O and C–S bond formation has been achieved from alcohols and p-toluenesulfonylmethyl isocyanide (TosMIC). Various alcohols reacted smoothly with TosMIC under the present conditions at room temperature providing sulfinate esters exclusively. By tuning the reaction temperature, the alcohols that provide highly stabilized carbocation in the reaction medium afforded sulfones as sole products. This study was aimed at understanding the regioselectivity of ambidentate sulfinate ion and to elucidate the interpretation of sulfinate/sulfone scaffolds.
Sulfination of Alcohols with p-Toluenesulfonylmethyl Isocyanide under Metal-Free Conditions: A Mitsunobu Approach
Kadari, Lingaswamy,Radha Krishna, Palakodety,Lakshmi Prapurna
supporting information, p. 3863 - 3868 (2016/12/16)
A Mitsunobu approach for the synthesis of sulfinate esters by direct nucleophilic substitution of alcohols is described. The salient features of this strategy include neutral and metal-free conditions for the rapid synthesis of sulfinates in high yields. The present protocol using p-toluenesulfonylmethyl isocyanide (TosMIC) and the triphenylphosphine (TPP)/diisopropyl azodicarboxylate (DIAD) reagent system represents the general synthetic route to this important class of compounds. (Figure presented.).
Sulfination of alcohols with sodium sulfinates promoted by BF3·OEt2: An unexpected access
Huang, Mingming,Hu, Liangzhen,Shen, Hang,Liu, Qing,Hussain, Muhammad Ijaz,Pan, Jing,Xiong, Yan
supporting information, p. 1874 - 1879 (2016/04/19)
A BF3·OEt2-promoted direct substitution of various alcohols with sodium sulfinates affording sulfinates under mild conditions has been developed. Further reaction of the hydroxysteroids achieves the highly complex sulfinates in good yields, which are two potential pharmacophores routinely encountered in drug discovery.
An efficient and novel method for the synthesis of sulfinate esters under solvent-free conditions
Hajipour, Abdol R.,Falahati, Ali R.,Ruoho, Arnold E.
, p. 2717 - 2719 (2007/10/03)
The present letter describes a reliable one-stage process for the preparation of sulfinate esters from the corresponding sulfinic acid and alcohols in the presence of N,N′-dicyclohexylcarbodiimide (DCC) under solvent-free conditions.
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.
