63268-44-0Relevant articles and documents
PhB(OH)2-Promoted Electrochemical Sulfuration-Formyloxylation of Styrenes and Selectfluor-Mediated Oxidation-Olefination
Zhao, Yulei,Guo, Xuqiang,Li, Shuai,Fan, Yuhang,Sun, Xuejun,Tian, Laijin
, p. 9140 - 9145 (2021/11/30)
We report a PhB(OH)2-promoted electrochemical sulfuration-formyloxylation reaction of styrenes employing commercially available thiophenols/thiols as thiolating agents. Specifically, metal catalysts and external chemical oxidants are not needed in the reaction for the formation of β-formyloxy sulfides, and these sulfides can be further converted to (E)-vinyl sulfones via the Selectfluor-mediated oxidation-olefination. Notably, on the basis of this electrochemical oxidation strategy, β-hydroxy sulfide, β-formyloxy sulfoxide, β-formyloxy sulfone, and (E)-vinyl sulfoxide can also be easily prepared.
Visible-light-induced selective synthesis of sulfoxides from alkenes and thiols using air as the oxidant
Cui, Huanhuan,Wei, Wei,Yang, Daoshan,Zhang, Yulong,Zhao, Huijuan,Wang, Leilei,Wang, Hua
supporting information, p. 3520 - 3524 (2017/08/15)
A highly selective synthesis of sulfoxides from alkenes and thiols was established by visible-light photoredox catalysis at room temperature. This metal-free transformation protocol, which uses inexpensive Rose Bengal as the photocatalyst and air as the green oxidant, opens a new door toward the facile and practical construction of sulfoxides.
(Diphenoxyphosphoryl)methyl p -tolyl sulfoxide: A new reagent for Z -selective synthesis of racemic and optically active vinyl sulfoxides
Midura, Wanda H.,Ewas, Ashraf M. Mohamed,Miko?ajczyk, Marian
, p. 535 - 540 (2016/04/05)
Racemic and optically active (+)-(S)-(diphenoxyphosphoryl)methyl p-tolyl sulfoxide were prepared and used as Horner olefination reagents. Their reaction with aromatic and aliphatic aldehydes afforded the corresponding racemic and enantiomeric α,β-unsatura
Metal-free, one-pot highly selective synthesis of (E)-vinyl sulfones and sulfoxides via addition-oxidation of thiols with alkynes
Xue, Qicai,Mao, Zhijie,Shi, Yan,Mao, Haibin,Cheng, Yixiang,Zhu, Chengjian
scheme or table, p. 1851 - 1854 (2012/04/23)
We have developed a highly selective one-pot method for the synthesis of (E)-vinyl sulfones and sulfoxides from thiols with terminal alkynes. The sulfones and sulfoxides could be obtained with excellent selectivity in good isolated yields. It is simple, e
Horner olefination reaction in organic sulfur chemistry and synthesis of natural and bioactive products
Mikolajczyk, Marian,Midura, Wanda H.,Mohamed Ewas, Ashraf M.,Perlikowska, Wieslawa,Mikina, MacIej,Jankowiak, Aleksandra
scheme or table, p. 313 - 325 (2009/04/06)
This article outlines the results of our work on the application of the Horner olefination reaction for the synthesis of unsaturated sulfur compounds. A general synthesis of racemic and optically-active α,β-unsaturated sulfoxides by the Horner reaction with α-sulfinylmethylphosphonates as olefination reagents is presented. We demonstrated how the structure of the phosphonate moiety may control the E- and Z-stereoselectivity in the above reaction. The use of racemic and optically-active α- sulfinylvinylphosphonates in tandem Michael addition/Horner olefination reaction leads to a wide range of carbocyclic and heterocyclic vinyl sulfoxides. In second part of this account a new strategy for the synthesis of functionalized cyclopentenones is briefly described. The synthesis and reactivity of 3-phosphorylmethyl-cyclopentenones is discussed as a platform for developing the synthesis of racemic rosaprostol, enantiomeric prostaglandin B1 methyl esters, enantiopure isoterreins, natural and unnatural neplanocin A and enantiomeric forms of phytoprostane B1 type I. Copyright Taylor & Francis Group, LLC.
Hydrotelluration and carbotelluration of acetylenic sulfoxides: Regio- and stereoselective preparation of α- and β-organotellurovinyl sulfoxides
Xu, Qing,Huang, Xian,Ni, Jun
, p. 2981 - 2984 (2007/10/03)
(Z)-β-Organotellurovinyl sulfoxides were synthesized via a highly regio- and stereoselective anti-hydrotelluration of acetylenic sulfoxides. α-Organotellurovinyl sulfoxides were obtained from a three component syn-carbotelluration reaction of acetylenic s
Studies on hydrozirconation of 1-alkynyl sulfoxides or sulfones and the application for the synthesis of stereodefined vinyl sulfoxides or sulfones
Huang, Xian,Duan, Dehui,Zheng, Weixin
, p. 1958 - 1963 (2007/10/03)
The hydrozirconation reaction of 1-alkynyl sulfoxides or sulfones with CP2Zr(H)Cl in THF at room temperature predominantly gave Z-β-zirconated vinyl sulfoxides or sulfones with excellent regioselectivity. Compared with 1-alkynyl sulfoxides, the hydrozirconation reaction of 1-alkynyl sulfones exhibits great synthetic potential, leading to the efficient preparation of Z-β-halovinyl sulfones, Z-β-sulfonyl α,β-unsaturated ketones, and Z-β-alkynyl vinyl sulfones. Although the reaction mechanisms are still not clear, the neighboring group participation of the sulfinyl or sulfonyl group may be playing an important role in this unique hydrozirconation reaction.
Hydrozirconation of alkynyl sulfoxides: The reactions of zirconated vinyl sulfoxide intermediates
Zhong, Ping,Huang, Xian,Ping-Guo, Meng
, p. 8921 - 8925 (2007/10/03)
Alkynyl sulfoxides react with Cp2Zr(H)Cl in THF at room temperature to give the α-zirconated and β-zirconated vinyl sulfoxides, which react with a wide range of electrophiles to give several types of di- or trisubstituted olefins, such as Z-vinyl sulfoxides and α- or β-halo vinyl sulfoxides. (C) 2000 Elsevier Science Ltd.
Simple and stereoselective synthetic route to (E)-1-alkenyl sulfoxides via terminal alkynes
Zhong,Guo,Huang
, p. 588 - 589 (2007/10/03)
Terminal alkynes 1 react with Cp2Zr(H)Cl (Cp = η5-C5H5) to give organozirconium (IV) complexes 2, which are trapped with sulfuryl chloride to afford (E)-1-alkenyl sulfoxides 3.
A novel sulfinylation of alkenes by tosyl cyanide with titanium(IV) chloride
Morgan, Paul E.,McCague, Ray,Whiting, Andrew
, p. 4857 - 4860 (2007/10/03)
Tosyl cyanide is activated by titanium(IV) chloride to generate a tolylsulfinyl chloride equivalent, which readily stereo- and regio- specifically adds to certain alkenes to provide β-chlorosulfoxides. These chlorides rapidly hydrolyse on silica gel to provide β-hydroxysulfoxides in stereocontrolled manner.