120344-44-7Relevant academic research and scientific papers
Manganese-Catalyzed N-Alkylation of Sulfonamides Using Alcohols
Reed-Berendt, Benjamin G.,Morrill, Louis C.
, p. 3715 - 3724 (2019/03/30)
An efficient manganese-catalyzed N-alkylation of sulfonamides has been developed. This borrowing hydrogen approach employs a well-defined and bench-stable Mn(I) PNP pincer precatalyst, allowing benzylic and simple primary aliphatic alcohols to be employed as alkylating agents. A diverse range of aryl and alkyl sulfonamides undergoes mono-N-alkylation in excellent isolated yields (32 examples, 85% average yield).
Nickel-catalyzed product-controllable amidation and imidation of sp3 C-H bonds in substituted toluenes with sulfonamides
Li, Ze-lin,Jin, Li-kun,Cai, Chun
supporting information, p. 1317 - 1320 (2017/02/15)
A nickel-catalyzed product-controllable imidation and amidation of sp3 C-H bonds in substituted toluenes with sulfonamides were developed. Based on the change of the reaction time and atmosphere from N2 to O2, this reaction proceeded in high yields and excellent selectivity under different conditions. Mechanistic details were also described.
Metal-free C-H sulfonamidation of pyrroles by visible light photoredox catalysis
Meyer, Andreas Uwe,Berger, Anna Lucia,K?nig, Burkhard
supporting information, p. 10918 - 10921 (2016/09/09)
We report a one-step procedure for the preparation of N-(2-pyrrole)-sulfonamides from sulfonamides and pyrroles. The reaction uses visible light, an acridinium dye as photocatalyst and oxygen as the terminal oxidant for the oxidative C-N bond formation; structures of several reaction products were confirmed by X-ray structure analysis. The reaction is selective for pyrroles, due to the available oxidation power of the photocatalyst and the required stability of the carbocation intermediate under the reaction conditions.
Diverse reactions of sulfonyl chlorides and cyclic imines
Liu, Jing,Hou, Shili,Xu, Jiaxi
experimental part, p. 2377 - 2391 (2012/04/04)
Although alkanesulfonyl chlorides react with linear imines to give rise to β-sultam derivatives, in this study, they were reacted with various cyclic imines, including 1-pyrroline, oxazoline, 5,6-dihydro-4H-oxazines and thiazines, 4,5-dihydro-3H-benzo[c]azepine, and 3,4-dihydroisoquinoline, to produce diverse products instead of β-sultam derivatives. The results indicate that alkanesulfonyl chlorides react with cyclic imines to generate N-alkanesulfonyl cyclic iminium ions, which are attacked by nucleophiles, such as water and chloride anion, in the reaction systems, affording addition products. The iminium intermediates cannot undergo a ring closure to form β-sultam derivatives. Arenesulfonyl chlorides showed similar behavior when they reacted with cyclic imines. The scope and limitation of the reaction between sulfonyl chlorides and imines were investigated. Copyright Taylor & Francis Group, LLC.
A reversible safety-catch method for the hydrogenolysis of N-benzyl moieties
Johnson II, David C.,Widlanski, Theodore S.
, p. 8483 - 8487 (2007/10/03)
The benzyl groups of β-hydroxy-N-benzyl sulfonamides are labile toward hydrogenolysis-unlike N-benzyl sulfonamides lacking the β-hydroxy moiety. We find that N-acyl-N-benzyl sulfonamides undergo hydrogenolysis under very mild conditions. Based upon these observations, we developed a reversible safety-catch method using tert-butoxycarbonyl moieties to activate N-benzyl sulfonamides toward hydrogenolysis. We also explored the utility of the safety-catch activation method for other nitrogen-based functionality such as N-benzyl carboxamides, imides, and related functionality.
Synthesis and reactivity of polydisulfonimides
Burlingham,Widlanski
, p. 2937 - 2945 (2007/10/03)
The first synthesis of alkyl disulfonimide oligomers is presented. In the process of synthesizing these oligomers, previously unreported reactivity of the N-substituted disulfonimide functional group was discovered. Under basic conditions, unexpected lengthening of the oligomers occurs through a "transdisulfonimidation" reaction, whereby new disulfonimides are synthesized from existing ones by reaction with sulfonamide anion. This process appears to proceed via formation of a sulfene intermediate. Support for the E1cBRev mechanism includes isotope scrambling, substituent effects, and sulfene trapping.
A Convenient Synthesis of 5-Substituted Tetrahydro-1,4,3-oxathiazine 4,4-Dioxides
Grunder-Klotz, Evelyne,Humbert, Paul,Ehrhardt, Jean-Daniel
, p. 733 - 742 (2007/10/02)
An adventageous one pot procedure for the synthesis of tetrahydro-1,4,3-oxathiazine 4,4-dioxides by dialkylation of readily available α,N-alkyl or arylsulfonamide dianions with gaseous formaldehyde is reported.Stability and some reactions of these heterocycles are also described.
