95196-99-9Relevant academic research and scientific papers
Electrochemical synthesis of sulfamides
Blum, Stephan P.,Sch?ffer, Lukas,Schollmeyer, Dieter,Waldvogel, Siegfried R.
, p. 4775 - 4778 (2021)
Herein we demonstrate the first electrochemical synthesis protocol of symmetrical sulfamides directly from anilines and SO2mediated by iodide. Sulfamides are an emerging functional group in drug design. Highlights are the direct use of SO2from a stock solution and no necessity of any supporting electrolyte. Overall, the reaction has been demonstrated for 15 examples with yields up to 93%.
Design and Applications of a SO2 Surrogate in Palladium-Catalyzed Direct Aminosulfonylation between Aryl Iodides and Amines
Jia, Xiuwen,Kramer, S?ren,Skrydstrup, Troels,Lian, Zhong
supporting information, p. 7353 - 7359 (2021/02/26)
A new SO2 surrogate is reported that is cheap, bench-stable, and can be accessed in just two steps from bulk chemicals. Essentially complete SO2 release is achieved in 5 minutes. Eight established sulfonylation reactions proceeded smoothly by ex situ formation of SO2 by utilizing a two-chamber system in combination with the SO2 surrogate. Furthermore, we report the first direct aminosulfonylation between aryl iodides and amines. Broad functional group tolerance is demonstrated, and the method is applicable to pharmaceutically relevant substrates, including heterocyclic substrates.
Vicinal Diamination of Arenes with Domino Aryne Precursors
Li, Lu,Qiu, Dachuan,Shi, Jiarong,Li, Yang
supporting information, p. 3726 - 3729 (2016/08/16)
Vicinal diamination of domino aryne precursors was achieved with sulfamides. The reaction proceeds through a two-aryne pathway, accepting two N-nucleophiles at the 1,2-positions of an arene ring. Symmetrical and unsymmetrical diaminobenzenes were readily obtained.
DABCO-bis (sulfur dioxide), DABSO, as a convenient source of sulfur dioxide for organic synthesis: Utility in sulfonamide and sulfamide preparation
Woolven, Holly,Gonzalez-Rodriguez, Carlos,Marco, Isabel,Thompson, Amber L.,Willis, Michael C.
supporting information; experimental part, p. 4876 - 4878 (2011/12/05)
The charge-transfer complex generated from the combination of DABCO and sulfur dioxide, DABSO, is a bench-stable colorless solid suitable for use in organic synthesis as a replacement for gaseous sulfur dioxide. The complex can be combined with Grignard reagents to form sulfinates, which can then be converted in situ to a series of sulfonamides. Alternatively, reaction with anilines and iodine leads to the formation of a series of sulfamides. Cheletropic addition between DABSO and 2,3-dimethylbutadiene provides the corresponding sulfolene.
Sulfamides and sulfamide polymers directly from sulfur dioxide
Leontiev, Alexander V.,Rasika Dias,Rudkevich, Dmitry M.
, p. 2887 - 2889 (2008/09/18)
SO2 gas is effectively used for the preparation of N,N′-diarylsulfamides and shape-persistent sulfamide polymers, which utilize a network of intermolecular N-H...O=S hydrogen bonds to self-assemble into soft porous materials. The Royal Society of Chemistry 2006.
