67723-10-8Relevant articles and documents
Cyanide-Mediated Synthesis of Sulfones and Sulfonamides from Vinyl Sulfones
Lee, Ji-Woong,Roy, Tamal
, p. 455 - 458 (2020)
We report a facile synthesis of sulfones, β-keto sulfones, and sulfonamides from vinyl sulfones via an addition-elimination sequence where in situ generation of nucleophilic sulfinate ion is mediated by cyanide. The use vinyl sulfones renders high selectivity for S -alkylation to produce sulfones in high yields. In the presence of N -bromosuccinimide, primary and secondary amines underwent sulfonamide formation. A preliminary mechanistic study showed the formation of acrylonitrile as an innocent byproduct, without interfering with the desired reaction pathway while generating a sulfinate nucleophile.
Copper-catalyzed electrophilic amination of sodium sulfinates at room temperature
Zhu, Haibo,Shen, Yajing,Deng, Qinyue,Tu, Tao
supporting information, p. 16573 - 16576 (2015/11/18)
By using O-benzoyl hydroxylamines as amine sources, the first convenient copper-catalyzed electrophilic amination of sodium sulfinates has been realized. Even with 2 mol% catalyst loading, the protocol provided an efficient and straightforward synthesis of a broad range of functional sulfonamides under ambient reaction conditions without an additional base and ligand. Based on the control experiments, a plausible mechanism was proposed.
Metal-free direct N-benzylation of sulfonamides with benzyl alcohols by employing boron trifluoride-diethyl ether complex
Pan, Jing,Li, Jia-Qiang,Huang, Ruo-Feng,Zhang, Xiao-Hui,Shen, Hang,Xiong, Yan,Zhu, Xiang-Ming
supporting information, p. 1101 - 1108 (2015/04/14)
N-Benzylation of sulfonamides with both primary and secondary benzyl alcohols by employing boron trifluoride-diethyl ether complex under mild reaction conditions has been developed, which is an environmentally benign and facile protocol for assembling a series of primary and secondary benzyl sulfonamides in yields up to 83%. In this coupling reaction, the beneficial role of water has been clarified in detail through control experiments.
Azodicarbonyl dimorpholide (ADDM): An effective, versatile, and water-soluble Mitsunobu reagent
Lanning, Maryanna E.,Fletcher, Steven
, p. 4624 - 4628 (2013/08/23)
One of the caveats of the Mitsunobu reaction is the often difficult and laborious purification of the reaction mixture. Herein, we show that azodicarbonyl dimorpholide (ADDM) is an effective and versatile Mitsunobu reagent, which, along with its reduced form ADDM-H2, may be removed from the reaction mixture by a simple aqueous extraction. Furthermore, we demonstrate that the isolated ADDM-H2 may be re-oxidized with silver(I) oxide to regenerate ADDM. Finally, a chromatography-free Mitsunobu reaction is presented.
Use of polymer supported reagents for clean multi-step organic synthesis: Preparation of amines and amine derivatives from alcohols for use in compound library generation
Ley, Steven V.,Bolli, Martin H.,Hinzen, Berthold,Gervois, Anne-Geraldine,Hall, Beverley J.
, p. 2239 - 2241 (2007/10/03)
The automated sequential application of polymer supported perruthenate (PSP) and polymer supported cyanoborohydride (PSCBH) in an oxidation-reductive amination procedure allowed the efficient transformation of simple alcohols into more complex amines which can be further derivatised by the use of polymer bound amino sulfonylpyridinium chlorides.
Reaction between N,N-Dialkylhydroxylamines and Sulphinyl Chlorides
Banks, Malcolm R.,Hudson, Robert F.
, p. 151 - 156 (2007/10/02)
The reactions of several N,N-dialkylhydroxylamines with methane- and benzene-sulphinyl chlorides below 0 deg C give O-sulphinylated intermediates.These rearrange at ambient temperatures to give the corresponding sulphonamides and in some cases the imines and products derived from the decomposition of the accompanying sulphinic acids.N.m.r. spectra ((1H and 13C) show strong polarizations in the sulphonamides, indicating a radical-cage mechanism.No CIDNP signals were observed in the imines, which can be formed in a six-electron symmetry-allowed cyclic elimination.
The Reaction between N,N-Dialkylhydroxylamines and Sulphinyl Chlorides
Banks, Malcolm R.,Hudson, Robert F.
, p. 799 - 800 (2007/10/02)
The reaction of N,N-dialkylhydroxylamines with sulphinyl chlorides proceeds via an O-sulphinylated hydroxylamine intermediate, which has been isolated and characterised by n.m.r. spectroscopy; rearrangement of this intermediate to the sulphonamide has been shown to involve an aminyl radical.
