69857-05-2Relevant articles and documents
NaHSO3-Mediated Direct Synthesis of Sulfinic Esters from Sulfonyl Hydrazides under Transition-Metal-Free Conditions
Zhang, Guofu,Fan, Qiankun,Wang, Huimin,Zhao, Yiyong,Ding, Chengrong
, p. 833 - 837 (2020/12/07)
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.).
Direct synthesis of sulfinic esters via ultrasound accelerated tandem reaction of thiols and alcohols with N-bromosuccinimide
Nguyen, Lan-Anh Thi,Le, Tri-Nghia,Duong, Cong-Thang,Vo, Chi-Tam,Duus, Fritz,Luu, Thi Xuan Thi
, p. 519 - 528 (2021/05/27)
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.
Metal- And oxidant-free electrochemical synthesis of sulfinic esters from thiols and alcohols
Ai, Chongren,Shen, Haiwei,Song, Dingguo,Li, Yujin,Yi, Xiao,Wang, Ze,Ling, Fei,Zhong, Weihui
supporting information, p. 5528 - 5531 (2019/10/22)
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.
Copper-Catalyzed Oxidative Reaction of β-Keto Sulfones with Alcohols via C?S Bond Cleavage: Reaction Development and Mechanism Study
Du, Bingnan,Wang, Wenmin,Wang, Yang,Qi, Zhenghang,Tian, Jiaqi,Zhou, Jie,Wang, Xiaochen,Han, Jianlin,Ma, Jing,Pan, Yi
supporting information, p. 404 - 408 (2018/02/21)
A Cu-catalyzed cascade oxidative radical process of β-keto sulfones with alcohols has been achieved by using oxygen as an oxidant. In this reaction, β-keto sulfones were converted into sulfinate esters under the oxidative conditions via cleavage of C?S bond. Experimental and computational studies demonstrate that a new pathway is involved in this reaction, which proceeds through the formation of the key four-coordinated CuII intermediate, O?O bond homolysis induced C?S bond cleavage and Cu-catalyzed esterification to form the final products. This reaction provides a new strategy to sulfonate esters and enriches the research content of C?S bond cleavage and transformations.
ORGANOSULPHUR COMPOUNDS-LXIX OPTICALLY ACTIVE SULPHINATES: A NEW TYPE OF ENANTIOSELECTIVE ASYMMETRIC SYNTHESIS AND KINETIC RESOLUTION
Drabowicz, Jozef,Legedz, Slawomir,Mikolajczik, Marian
, p. 5243 - 5252 (2007/10/02)
Optically active sulphinates with the sulphur atom as a sole centre of chirality are prepared by two methods.The first involves the reaction of symmetrical sulphites with tert-butylmagnesium chloride in the presence of optically active aminoalcohols.This new asymmetric, enantioselective synthesis affords t-butylsulphinates with 40-70percent enantiomeric excess values.The second approach is based on a new type of kinetic resolution taking place when racemic sulphinates are reacted with tert-butylmagnesium chloride complexed by optically active alkaloid bases.Both the recovered sulphinates and sulphoxides formed in this reaction show moderate optical purities.
