- Rearrangement Reaction Based on the Structure of N-Fluoro- N-alkyl Benzenesulfonamide
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A novel rearrangement reaction based on the structure of N-fluoro-N-alkyl benzenesulfonamide was developed. The reaction proceeded readily at 50 °C in formic acid and generated a variety of benzenesulfonamides and aldehydes or ketones simultaneously. The reaction mechanism is believed to be a concerted mechanism that consist of 1,2-aryl migration with the departure of fluorine anion via an SN2 mechanism. This rearrangement reaction features an interesting reaction mechanism, mild reaction conditions, simple operations, and a broad substrate scope.
- Wang, Han-Ying,Pu, Xiao-Qiu,Yang, Xian-Jin
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p. 13103 - 13110
(2018/10/20)
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- Palladium-catalyzed desulfitative arylation of sulfonamides with sodium arylsulfinates
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A Pd(II)-catalyzed desulfitative arylation protocol between sulfonamides and sodium arylsulfinates was herein reported. The direct arylation reaction was successfully achieved by a Pd(II)/Ag(I)-mediated system without participation of any external ligands with a release of SO2. And different N-aryl sulfonamides were obtained readily in up to 86% yields, exhibiting good functional groups tolerance (25 examples).
- Zhao, Zijian,Lian, Yan,Zhao, Chang,Wang, Bing
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supporting information
p. 1436 - 1442
(2018/06/01)
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- A convenient and benign synthesis of sulphonamides in PEG-400
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A simple and convenient method is reported for the synthesis of a series of sulphonamides in PEG-400 using potassium carbonate as the base. The reaction is carried out in a heterogeneous medium and consequently product recovery is simple. The desired products with a variety of aromatic amines could be synthesized in a short reaction time in good yield. The PEG could be recovered for reuse.
- Das, Pranab Jyoti,Sarmah, Bhaskar
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p. 189 - 191
(2015/02/19)
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- Synthetic use of 1,1,2,2-tetraphenyldisilane for the preparation of biaryls through the intramolecular free radical ipso-substitution of N-(2-bromoaryl)arenesulfonamides
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Treatment of various N-methyl-N-(2-bromoaryl)arenesulfonamides (1a-g, 1i, and 1m) with 1,1,2,2-tetraphenyldisilane and AIBN under heating conditions gave the corresponding biaryl products (2a-g, 2i, and 2m) in moderate yields through the intramolecular radical ipso-substitution. However, N-H free N-(2-bromoaryl)arenesulfonamides 1h and 2-bromoaryl arenesulfonate 1j did not give the corresponding biarys. 1,1,2,2-Tetraphenyldisilane is the most effective reagent for 1,5-ipso-substitution on the sulfonamides among typical radical reagents such as diphenylsilane, tributyltin hydride, tris(trimethylsilyl)silane, and 1,1,2,2-tetraphenyldisilane. Furthermore, 1,1,2,2-tetraphenyldisilane has the advantages of low toxicity, stability, and ease of preparation.
- Ryokawa, Atsushi,Togo, Hideo
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p. 5915 - 5921
(2007/10/03)
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- α-fluoromethyl tryptophans via imino ene reaction
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A preparative simple synthesis of α-fluoromethyl tryptophans is described. The new method is based on a non-catalytic imine ene reaction of highly electrophilic imines derived from methyl bromodifluoro- and trifluoropyruvate, and 1-sulfonyl-3-methylene in
- Osipov,Kobel'Kova,Kolomiets,Pumpor,Koksch,Burger
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p. 1287 - 1289
(2007/10/03)
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- Chiral sulfoxide ligands bearing nitrogen atoms as stereocontrollable coordinating elements in palladium-catalyzed asymmetric allylic alkylations
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Palladium-catalyzed asymmetric allylic alkylations were studied by using chiral sulfoxide ligands bearing nitrogen atoms as coordinating elements, such as chiral α-sulfinylacetamides, β or γ-amino sulfoxides, and β- sulfinyl sulfonamides. The effects of t
- Hiroi, Kunio,Suzuki, Yoshio,Abe, Ikuko,Hasegawa, Yutaka,Suzuki, Kenji
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p. 3797 - 3817
(2007/10/03)
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- Kinetische Verfolgung der Sulfamidbildung mittels quantitativer Differentialthermoanalyse
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Die Reaktion zwischen Benzolsulfochlorid und einigen Anilinderivaten kann im Bereich oberchalb 200 K mit der dynamischen Technik der DTA untersucht werden, wobei sich eine Reaktion 2.Ordnung ergibt.Aktivierungsparameter und Reaktionsenthalpien werden durch die Anilinsubstituenten beeinflusst.
- Anderson, H.,Hoffmann, U.,Haberland, D.
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p. 639 - 648
(2007/10/02)
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