49557-76-8Relevant academic research and scientific papers
Sulfinate-Organocatalyzed (3+2) Annulation Reaction of Propargyl or Allenyl Sulfones with Activated Imines
Martzel, Thomas,Lohier, Jean-Fran?ois,Gaumont, Annie-Claude,Brière, Jean-Fran?ois,Perrio, Stéphane
supporting information, p. 5069 - 5073 (2018/09/14)
An operationally simple methodology for the synthesis of 4-sulfonyl-3-pyrrolines is described using a propargylic sulfone and N-sulfonyl imines as substrates. This annulation process is initiated by an arenesulfinate organocatalyst, which allows a smooth isomerization of the alkynyl precursor into the corresponding allene, followed by the generation of a highly reactive allyl sulfone anion. An asymmetric version involving an unprecedented enantiopure sulfinate–ammonium cooperative ion pair (PhSO2– R4N+*) was investigated. A proof-of-concept, with enantiomeric excesses of up to 41 %, was obtained according to a preliminary screening of commercially available chiral phase-transfer catalysts.
Synthesis of 3-(Arylsulfonyl)-3-pyrrolines from Allenyl Sulfonamides by Silver Ion Catalysis
Tata, Rama Rao,Fu, Chencheng,Kelley, Steven P.,Harmata, Michael
supporting information, p. 5723 - 5726 (2018/09/21)
Treatment of allenyl sulfonamides with catalytic amounts of silver fluoride in acetonitrile at reflux afforded the corresponding 3-sulfonyl-3-pyrrolines in excellent yields by intramolecular hydroamination via a 5-endo-trig cyclization. The starting allenyl sulfonamides were prepared by lithiation of allenic sulfones and trapping with various N-sulfonylimines.
Nitroxyl-Radical-Catalyzed Oxidative Coupling of Amides with Silylated Nucleophiles through N-Halogenation
Moriyama, Katsuhiko,Kuramochi, Masako,Fujii, Kozo,Morita, Tsuyoshi,Togo, Hideo
supporting information, p. 14546 - 14551 (2016/11/23)
A nitroxyl-radical-catalyzed oxidative coupling reaction between amines with an N-protecting electron-withdrawing group (EWG) and silylated nucleophiles was developed to furnish coupling products in high yields, thus opening up new frontiers in organocatalyzed reactions. This reaction proceeded through the activation of N-halogenated amides by a nitroxyl-radical catalyst, followed by carbon–carbon coupling with silylated nucleophiles. Studies of the reaction mechanism indicated that the nitroxyl radical activates N-halogenated amides, which are generated from N-EWG-protected amides and a halogenation reagent, to give the corresponding imines.
Synthesis of N-Sulfonyl Arylaldimines Developed by Retesting an Old Process
Huang, Dayun,Wang, Xuesong,Wang, Xingyong,Chen, Wenwen,Wang, Xinyan,Hu, Yuefei
supporting information, p. 604 - 607 (2016/02/18)
By simply heating the mixture of an arylaldehyde and a sulfonylisocyanate in a solvent or in neat form under catalyst- and additive-free conditions, the desired N-sulfonylimine was produced with the release of carbon dioxide. The method is characterized b
Original synthesis of 2-substituted-4,11-dimethoxy-1-(phenylsulfonyl)-2,3- dihydro-1H-naphtho[2,3-f]indole-5,10-diones using TDAE and Cu-catalyzed reaction strategy
Khoumeri, Omar,Giuglio-Tonolo, Gamal,Crozet, Maxime D.,Terme, Thierry,Vanelle, Patrice
scheme or table, p. 6173 - 6180 (2011/09/19)
We report herein an original and rapid synthesis of 2-substituted-4,11- dimethoxy-1-(phenylsulfonyl)-2,3-dihydro-1H-naphtho[2,3-f]indole-5,10-diones by TDAE mediated synthesis of N-benzylsulfonamides followed by an intramolecular N-arylation using Cu-catalyzed system.
Highly efficient and diastereoselective synthesis of 1,3-oxazolidines featuring a palladium-catalyzed cyclization reaction of 2-butene-1,4-diol derivatives and imines
Chen, Dongxu,Chen, Xiaoyi,Du, Taiping,Kong, Lichun,Zhen, Renwei,Zhen, Shaocheng,Wen, Yihang,Zhu, Gangguo
supporting information; experimental part, p. 5131 - 5133 (2010/11/18)
A palladium-catalyzed protocol for effective synthesis of 1,3-oxazolidines has been reported. This method is featured by the high diastereoselectivity (dr up to >98/2) and using the readily available 2-butene-1,4-diol derivatives and imines as substrates.
Gold-catalyzed synthesis of 2-aryl-3-fluoropyrroles
Surmont, Riccardo,Verniest, Guido,De Klmpe, Norbert
scheme or table, p. 2920 - 2923 (2009/12/05)
The gold-catalyzed cyclizatlon and dehydrofluorination of gem-dlfluorohomopropargylamlnes provides a novel access to 2-aryl-3- fluoropyrroles. Difluorinated homopropargylamines are prepared by the addition of gem-difluoropropargyllithium reagents to aryla
Preparation of N-arylsulfonyl imines from sulfonamides and aryl aldehydes using magnesium oxide as a heterogeneous and reusable catalyst under solvent-free conditions
Hasaninejad, Alireza,Zare, Abdolkarim,Zare, Ahmad Reza Moosavi,Parhami, Abolfath,Sharghi, Hashem,Khalafi-Nezhad, Ali
experimental part, p. 2769 - 2776 (2009/09/06)
An efficient solvent-free procedure for the preparation of N-arylsulfonyl imines from sulfonamides and aryl aldehydes in the presence of a catalytic amount of magnesium oxide and tetrabutylammonium bromide (TBAB) under microwave irradiation is described. The advantages of this method are good to high yields, short reaction times, low cost, and matching with green chemistry protocols. Copyright Taylor & Francis Group, LLC.
A novel method for the synthesis of N-sulfonylaldimines by ZnO as a recyclable neutral catalyst under solvent-free conditions
Hosseini-Sarvari, Mona,Sharghi, Hashem
, p. 2125 - 2130 (2008/02/08)
ZnO acts as an effective catalyst for the rapid synthesis of a range of N-sulfonylaldimines from aromatic aldehydes and sulfonamides under solvent free conditions. The ZnO powder can be reused up to three times after simple washing with distilled water and ethyl acetate.
Efficient and convenient procedure for preparation of N-sulfonylimines catalyzed by montmorillonite K-10
Jin, Tong-Shou,Yu, Mi-Jun,Liu, Li-Bin,Zhao, Ying,Li, Tong-Shuang
, p. 2339 - 2344 (2007/10/03)
A general and practical chemical route to the synthesis of N-sulfonylimines using montmorillonite K-10 as the catalyst is described. This method provides several advantages such as operational simplicity, short reaction time, using of inexpensive materials, noncorrosivity, lack of pollution, and high yields. Copyright Taylor & Francis Group, LLC.
