837-18-3Relevant articles and documents
A Strategy to Control the Reactivation of Frustrated Lewis Pairs from Shelf-Stable Carbene Borane Complexes
Hoshimoto, Yoichi,Kinoshita, Takuya,Ohashi, Masato,Ogoshi, Sensuke
, p. 11666 - 11671 (2015)
N-Phosphine oxide substituted imidazolylidenes (PoxIms) have been synthesized and fully characterized. These species can undergo significant changes to the spatial environment surrounding their carbene center through rotation of the phosphine oxide moiety. Either classical Lewis adducts (CLAs) or frustrated Lewis pairs (FLPs) are thus formed with B(C6F5)3 depending on the orientation of the phosphine oxide group. A strategy to reactivate FLPs from CLAs by exploiting molecular motions that are responsive to external stimuli has therefore been developed. The reactivation conditions were successfully controlled by tuning the strain in the PoxIm-B(C6F5)3 complexes so that reactivation only occurred above ambient temperature. Frustration under control: Imidazolylidenes with a phosphine oxide substituent on one of the nitrogen atoms can undergo drastic changes to the spatial environment surrounding their carbene center through rotation of the phosphine oxide moiety. Depending on the orientation of this group, either classical Lewis adducts or frustrated Lewis pairs (FLPs) are formed upon addition of B(C6F5)3.
Synthesis of Polysubstituted Fused Pyrroles by Gold-Catalyzed Cycloisomerization/1,2-Sulfonyl Migration of Yndiamides
Smith, Philip J.,Jiang, Yubo,Tong, Zixuan,Pickford, Helena D.,Christensen, Kirsten E.,Nugent, Jeremy,Anderson, Edward A.
supporting information, p. 6547 - 6552 (2021/08/30)
Yndiamides (bis-N-substituted alkynes) are valuable precursors to azacycles. Here we report a cycloisomerization/1,2-sulfonyl migration of alkynyl-yndiamides to form tetrahydropyrrolopyrroles, unprecedented heterocyclic scaffolds that are relevant to medicinal chemistry. This functional group tolerant transformation can be achieved using Au(I) catalysis that proceeds at ambient temperature, and a thermally promoted process. The utility of the products is demonstrated by a range of reactions to functionalize the fused pyrrole core.
Synthetic method for catalyzing imine to be reduced into amine
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Paragraph 0076-0078, (2021/04/14)
The invention discloses a synthesis method for catalyzing imine to be reduced into amine, wherein the synthesis method is characterized by comprising the following steps: 1, sequentially putting a sulfonyl imine compound and a catalyst I into a reaction bottle according to a reaction molar ratio of 1:0.01 at normal temperature and normal pressure, adding formic acid and a triethylamine solution according to a volume ratio of 5:2, and reacting in a solvent for 1-15 minutes to obtain a reaction product; and 2, after the reaction in the step 1 is finished, sequentially and slowly adding water and ethyl acetate into an obtained reaction product, sufficiently stirring, standing for layering, extracting a separated water layer by using ethyl acetate, combining an extract of ethyl acetate with a separated organic layer, washing by using saturated edible salt water, and drying by using anhydrous sodium sulfate, evaporating to remove the ethyl acetate solvent to obtain a crude product, and separating and purifying by silica gel column chromatography to obtain the amine compound.
Implication of a Silyl Cobalt Dihydride Complex as a Useful Catalyst for the Hydrosilylation of Imines
Barbazanges, Marion,Bories, Cassandre C.,Derat, Etienne,Petit, Marc
, p. 14262 - 14273 (2021/11/27)
Here, we describe the formation and use of silyl cobalt (III) dihydride complexes as powerful catalysts for the hydrosilylation of a variety of imines starting from a low-valent well-defined cobalt (I) complex. The reaction is efficient at low catalyst loadings with a diverse range of imines bearing various protecting groups, as well as aliphatic ketimines and quinoline. Kinetics, DFT calculations, NMR spectroscopic studies, deuteration experiments, and X-ray diffraction analyses allowed us to propose a catalytic cycle based on silyl dihydrocobalt (III) complexes performing a hydrocobaltation.
Amide Iridium Complexes As Catalysts for Transfer Hydrogenation Reduction of N-sulfonylimine
Wen, Huiling,Luo, Nianhua,Zhu, Qianheng,Luo, Renshi
, p. 3850 - 3859 (2021/03/09)
Sulfonamide moieties widely exist in natural products, biologically active substance, and pharmaceuticals. Here, an efficient water-soluble amide iridium complexes-catalyzed transfer hydrogenation reduction of N-sulfonylimine is developed, which can be carried out under environmentally friendly conditions, affording a series of sulfonamide compounds in excellent yields (96-98%). In comparison with organic solvents, water is shown to be critical for a high catalytic transfer hydrogenation reduction in which the catalyst loading can be as low as 0.001 mol %. These amide iridium complexes are easy to synthesize, one structure of which was determined by single-crystal X-ray diffraction. This protocol gives an operationally simple, practical, and environmentally friendly strategy for synthesis of sulfonamide compounds.
AEROBIC OXIDATIVE SYNTHESIS OF SULFONAMIDE USING Cu CATALYST
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Paragraph 0033-0037; 0039-0054; 0129-0131, (2021/04/06)
The present invention relates to a method for oxidative synthesis of sulfonamides using copper catalysts. , Oxygen (O) is used. 2 The oxidative synthesis of sulfonamides (1) comprises reacting a 2 th or sulfonyl hydrazide primary amine with a sulfonyl hydrazide (sulfonamide) with a copper catalyst on a solvent under the conditions in which the sulphonamide is fed. The oxidation coupling of the present invention showed extensive substrate ranges in an amine comprising a 2 primary amine, 1 primary amine and amine hydrochloride salt. It is worth notable that non-reactive aliphatic sulfonyl hydrazides in previously reported anaerobic systems can be used for the aerobic oxidation coupling of the present invention. The oxidation coupling of the present invention has been more effective on large scale.
Preparation method of nitrogen-substituted sulfonamide compound
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Paragraph 0031-0038, (2020/04/02)
The invention discloses a preparation method of a nitrogen-substituted sulfonamide compound, and belongs to the field of organic synthesis. The nitrogen-substituted sulfonamide compound as shown in aformula (I) is prepared by directly coupling an aryl sulfonamide compound as shown in a formula (II) and a p-toluenesulfonylhydrazone compound as shown in a formula (III) under the action of a specific copper catalyst, an alkali reagent and an additive without ligand participation and a high-temperature reaction system. According to the method, the raw materials are cheap and easy to obtain, the reaction process is green, simple and convenient, and the yield of the nitrogen-substituted sulfonamide compound can reach 76%.
Electrochemical synthesis of sulfonamides in a graphite powder macroelectrode
Galdino, Danilo,Menezes, Paulo H.,Navarro, Marcelo,Vicente, Dmistocles A.
supporting information, p. 5262 - 5266 (2020/09/17)
The electrochemical generation of sulfinyl radicals from commercially available and non-expensive sodium salts of sulfinic acids is described. Electrooxidation reactions were carried out in a graphite powder macroelectrode using an aqueous electrolyte and cavity cell. Further reaction with primary or secondary amines gave the corresponding sulfonamides, a unit present in several biologically active compounds and pharmaceuticals, in good yields.
Cyanide-Mediated Synthesis of Sulfones and Sulfonamides from Vinyl Sulfones
Lee, Ji-Woong,Roy, Tamal
, p. 455 - 458 (2020/03/13)
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.
Efficient and Practical Synthesis of Sulfonamides Utilizing SO2 Gas Generated on Demand
Chung Leung, Gulice Yiu,Ramalingam, Balamurugan,Loh, Gabriel,Chen, Anqi
, p. 546 - 554 (2020/04/22)
A simple and practical protocol was developed for the synthesis of sulfonamides by reacting organometallic reagents with SO2 gas generated on demand. SO2 was generated from readily available reagents safely in a highly contained and controlled fashion. The protocol allows the synthesis of sulfonamides without using either atom-inefficient SO2 surrogates or a SO2 cylinder that requires stringent storage regulations in the laboratory. The protocol was successfully applied to the synthesis of sildenafil.
