- Debenzylative Sulfonylation of Tertiary Benzylamines Promoted by Visible Light
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An efficient, general, inexpensive, and environmentally friendly photosynthesis of sulfonamides via visible light promoted debenzylative sulfonylation of tertiary benzylamines is described. Compared to the traditional S?N coupling reactions, which are promoted by oxidative C?N bond cleavage of symmetrical tertiary alkylamines, this strategy provides a selective C?N bond cleavage protocol and avoids the use of transition-metal, explosive oxidants, and ligands.
- Fu, Ying,Wu, Qing-Kui,Du, Zhengyin
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supporting information
p. 1896 - 1900
(2021/04/06)
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- Synthesis method of aryl tertiary sulfonamide compound
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The invention provides a synthesis method of an aryl tertiary sulfonamide compound. In an aprotic solvent, with aryl sulfonyl chloride and a N,N-disubstituted-4-oxopiperidine quaternary ammonium saltcompound as raw materials and N-methylmorpholine as alka
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Paragraph 0032; 0033
(2019/10/01)
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- Double C-N bond cleavages of: N-alkyl 4-oxopiperidinium salts: Access to unsymmetrical tertiary sulfonamides
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In this paper, regiospecific, double intraannular C-N bond cleavages of N-alkyl 4-oxopiperidinium salts are presented. The reaction sequence involves a charge-transfer complex, in situ formed between sulfonyl chloride and N-methylmorpholine, which induces S-Cl bond homolysis of sulfonyl chloride, yielding a reactive sulfonyl radical that further induces the double C-N bond cleavages of N-alkyl 4-oxopiperidinium salt. The secondary amine thus produced was trapped by sulfonyl chloride to yield the desired sulfonamide product. The key feature of this protocol is that two intraannular C-N bonds of the 4-oxopiperidine ring are cleaved in one step under metal- A nd oxidant-free conditions.
- Fu, Ying,Li, Ming-Peng,Shi, Chun-Zhao,Li, Fang-Rong,Du, Zhengyin,Huo, Congde
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p. 10172 - 10177
(2019/12/26)
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- Visible-Light-Mediated Amination of π-Nucleophiles with N-Aminopyridinium Salts
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N-Aminopyridinium salts generate nitrogen-centered radicals by means of photoredox catalysis. Herein, we report that they can be trapped by enol equivalents to give α-amino carbonyl compounds in excellent yields. The broad synthetic utility of this method is demonstrated by functionalization of ketones, aldehydes, esters enol equivalents, vinyl ethers, and 1,3-diketones without the need for prior conversion to enol derivatives. The developed method is easily scalable, offers broad substrate scope, high chemoselectivity.
- Goliszewska, Katarzyna,Rybicka-Jasińska, Katarzyna,Szurmak, Jakub,Gryko, Dorota
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p. 15834 - 15844
(2019/11/03)
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- Solar-driven incorporation of carbon dioxide into α-amino ketones
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Power of the sun: Carbon dioxide was incorporated into α-amino ketones through a consecutive process consisting of a solar-energy-harvesting photocyclization reaction and a nucleophilic CO2 incorporation reaction. The single-flask operation produced amino-substituted cyclic carbonates, thereby presenting a simple model of the chemical utilization of solar energy for CO2 incorporation. R=sulfonyl group. Copyright
- Ishida, Naoki,Shimamoto, Yasuhiro,Murakami, Masahiro
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supporting information
p. 11750 - 11752
(2013/01/15)
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- OXIDATION OF 1-PHENYL-2-(N-METHYL-p-TOLUENESULFAMIDO)ETHANOL WITH AN OZONE-AIR MIXTURE.
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The results of further studies of the process of oxidation of secondary aliphatic-aromatic alcohols by ozone based on the example of 1-phenyl-2-(N-methyl-p-toluenesulfamido)-ethanol, an intermediate product in the synthesis of ephedrine, are reported. As a result of the studies conducted, it was found that the secondary alcohol studied can also be oxidized by molecular oxygen in the experimental conditions, and the corresponding ketone is formed with a yield of 20%. It is shown that the corresponding ketone is formed with a yield of 68% in the oxidation of 1-phenyl-2-(N-methyl-p-toluenesulfamido)ethanol by an ozone-air mixture in a medium of carbon tetrachloride. The yield of the ketone increases to 98% in the presence of an inhibitor of destructive oxidation of the aromatic ring, formaldehyde.
- Galstyan,Galstyan,Yakobi
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p. 2474 - 2478
(2007/10/02)
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- Removal of Toluene-p-sulphonyl Groups from Sulphonamides. Part 4. Synthesis of Phenylglyoxal Imine Monomers
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Syntheses and reactions of N-tosylphenacylamines with bases have been systematically examined.Monomeric C-methoxy-imines are available from some of these reactions.C-Methoxyphenacylarylamines, made by two routes, were converted into monomeric imines on treatment with noble-metal catalysts, The boron trifluoride-catalysed reactions of aryl aldehydes with sulphonamides provide a new and convenient route to N-sulphonylarylimines.
- McKay, William R.,Proctor, George R.
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p. 2435 - 2442
(2007/10/02)
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- N-Acyl-3-azetidinone
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Disclosed herein are novel N-acyl-3-aryl-3-azetidinols useful as intermediates. A method is provided for their direct preparation from acyclic starting materials. These N-acyl-3-aryl-azetidinols provide a convenient route to the 3-azetidinol series.
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