10399-00-5Relevant academic research and scientific papers
Practical N-hydroxyphthalimide-mediated oxidation of sulfonamides to N-sulfonylimines
Wang, Jian,Yi, Wen-Jing
, (2019)
A new method to prepare sulfonylimines through the oxidation of sulfonamides mediated by N-hydroxyphthalimide under mild conditions has been developed. Compared to reported oxidation methods, broader substrates scope and milder conditions were achieved in
A simple method for the preparation of N-sulfonylimines by direct condensation of p-toluenesulfonamide with diaryl ketones
Ram, Ram N.,Khan, Arif Ali
, p. 841 - 846 (2001)
Diaryl ketones condense with p-toluenesulfonamide in refluxing 1,2-dichloroethane in the presence of TiCl4/ Ti(O-iPr)4 or TiCl4/Et3N to give N-sulfonylimines in generally good yields.
Preparation and Reactions of Titanium(III) Chloride Solubilized in Inert Organic Solvents
Suzuki, Hitomi,Manabe, Hajime,Enokiya, Rika,Hanazaki, Yasuaki
, p. 1339 - 1340 (1986)
Titanium(IV) chloride reacts with dialkyl telluride in inert solvents such as dichloromethane or benzene to form a stable homogeneous solution of titanium(III) species.Reduction of several organic functionalities has been carried out using the low valent
Synthesis of N-sulfonylimines using CeCl3 under neutral conditions
Zhu, Xun,Wei, Yunyang
, p. 363 - 364 (2012)
An efficient and environmentally benign method for the synthesis of N-sulfonylimines is reported. Condensation of aryl sulfonamides with different aromatic aldehydes and ketones gave N-sulfonylimines in good to excellent yields in the presence of 10 mol% CeCl3 as catalyst. This method can be used with both aldehydes and ketones.
Chiral Bifunctional Phosphine Ligand Enables Gold-Catalyzed Asymmetric Isomerization and Cyclization of Propargyl Sulfonamide into Chiral 3-Pyrroline
Cheng, Xinpeng,Zhang, Liming
supporting information, p. 8194 - 8198 (2021/11/01)
This work details an asymmetric gold-ligand cooperative catalysis that transforms readily accessible chiral/achiral propargylic sulfonamides into chiral 3-pyrrolines. A bifunctional biphenyl-2-ylphosphine ligand featuring a chiral tetrahydroisoquinoline fragment is essential for the observed metal-ligand cooperation and the asymmetric induction. 2,5-cis-3-Pyrrolines are formed with excellent diastereoselectivities in a matched scenario. The mismatched scenario by using the ligand enantiomer delivers 2,5-trans-3-pyrrolines with >5/1 diastereoselectivity. The synthetic utilities of this chemistry are demonstrated.
5-(Diarylimino)- And 5-(sulfoximido)dibenzothiophenium triflates: syntheses and applications as electrophilic aminating reagents
Li, Zhen,Vijaykumar, Gonela,Li, Xiangdong,Golz, Christopher,Alcarazo, Manuel
supporting information, p. 2941 - 2948 (2021/04/14)
The one-pot synthesis of well-defined 5-(diarylimino) and 5-(sulfoximido)dibenzothiophenium triflates, respectively from diarylimines or sulfoximines, is reported and the structures of a series of these compounds are elucidated by X-ray crystallography. In analogy to their hypervalent I(iii) analogues, the iminoyl and sulfoximidoyl groups of these compounds can be selectively transferred to organic substrates. Specifically, the uncatalyzed imination of thiols or sulfinates proceeds with good yields, while under the mild reaction conditions offered by visible light photoredox catalysis, the radical amination of hydrazones or the sulfoximidation of benzylic, allylic and propargylic C-H bonds takes place satisfactorily.
Methyltrioxorhenium/urea hydrogen peroxide catalyzed oxidation of N-sulfinyl imines: A mild and highly efficient access to N-sulfonyl aldimines, ketimines and α-ketiminoesters
Tan, Yu,Ma, Ru-Lin,Lin, Hua,Sun, Xing-Wen
supporting information, (2020/11/25)
A mild and highly efficient access to N-sulfonyl imines through the oxidation of corresponding N-tert-butylsulfinyl imines and N-p-tosyl-sulfinyl imines with UHP in the presence of catalytic amount MTO was developed. Under mild reaction conditions, this h
Direct Synthesis of Enolizable N-Sulfonyl Ketimines under Microwave Irradiation
Ortiz, Pablo,Collados, Juan F.,Harutyunyan, Syuzanna R.
supporting information, p. 1247 - 1250 (2016/03/19)
N-sulfonyl imines are widely used as substrates for a range of transformations. Access to N-sulfonyl aldimines is straightforward through direct condensation between the parent aldehyde and the sulfonamide. However, this approach is not efficient for the
Reduction of sulfonylimines with raney nickel
Ruano, Jose Luis Garca,Fernandez-Salas, Jose A.,Maestro, M. Carmen,Parra, Alejandro
, p. 198 - 207,10 (2020/09/02)
Raney-Ni/EtOH reduction of different N-sulfonylimines provides a new entry for synthesizing sulfonamides in good yields under mild conditions. This protocol, which does not require additional hydrogen, constitutes a cheap, safe, and easy-to-handle alterna
Triarylmethyl chlorides as novel, efficient, and mild organic catalysts for the synthesis of N-sulfonyl imines under neutral conditions
Khalafi-Nezhad, Ali,Parhami, Abolfath,Zare, Abdolkarim,Shirazi, Amir Nasrolahi,Zare, Ahmad Reza Moosavi,Hassanimejad, Alireza
, p. 456 - 461 (2008/09/20)
A highly efficient procedure for the preparation of N-sulfonyl imines via condensation of sulfonamides with aldehydes as well as ketones in the presence of triarylmethyl chlorides as metal-free organo-catalysts at 40 °C is described. The advantages of thi
