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1.
Andreas Uwe Meyer Karolína Straková Dr. Tomáš Slanina Prof. Dr. Burkhard König 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(25):8694-8699
Alkyl‐ and aryl vinyl sulfones were obtained by eosin Y (EY)‐mediated visible‐light photooxidation of sulfinate salts and the reaction of the resulting S‐centered radicals with alkenes. Optimized reaction conditions, the sulfinate and alkene scope, and X‐ray structural analyses of several reaction products are provided. A detailed spectroscopic study explains the reaction mechanism, which proceeds through the EY radical cation as key intermediate oxidizing the sulfinate salts. 相似文献
2.
José L. García Ruano Alejandro ParraLeyre Marzo Francisco YusteVirginia M. Mastranzo 《Tetrahedron》2011,67(16):2905-2910
Room temperature ultrasonic irradiation of neat mixtures of methyl sulfinates and primary or secondary amines (1.5 equiv) produced sulfinamides, which on m-CPBA oxidation (in dichloromethane) were converted into the corresponding sulfonamides. The two steps can be accomplished in one pot, in good overall yields, when using secondary amines, but primary amines give better sulfonamide yields when the peracid oxidation is effected on the purified sulfinamide. This constitutes a mild, efficient, and potentially scalable route to sulfonamides, which obviates the use of water sensitive, often lachrymatory sulfonyl chlorides and large reagent excesses. 相似文献
3.
Laure C. Bouchez 《Tetrahedron》2005,61(48):11473-11487
In previous papers (Synthesis2002, 232 and J. Org. Chem.2004, 69, 6413), we have shown that the hetero-Diels-Alder addition of sulfur dioxide to 1-oxy or 1,3-dioxy-1,3-dienes generates zwitterions that add to enoxysilanes or allylsilanes giving silyl sulfinates that can be converted in the same pot into polyfunctional sulfones, sulfonamides or sulfonic esters. We are presenting further applications of this method, including the synthesis of new medium-size heterocyclic systems of the type tetrahydro-2H-thiocines and hexahydro-1,2-thiazonine. 相似文献
4.
5.
《Tetrahedron letters》2019,60(46):151260
It was reported to develop a simple and convenient method for the Ni/NHC-catalyzed cross-coupling of methyl sulfinates and amines without an acid/base to afford secondary or tertiary sulfinamides in moderate to good yields. The method can provide the desired products with broad substrate scope, good chemoselectivity and good functional group compatibility. The presented approach may enrich the Ni/NHC catalyst system and promote the applications of methyl sulfinates in the organic sulfur chemistry. 相似文献
6.
Julien Coulomb Victor Certal Dr. Marie‐Hélène Larraufie Cyril Ollivier Dr. Jean‐Pierre Corbet Dr. Gérard Mignani Dr. Louis Fensterbank Prof. Emmanuel Lacôte Dr. Max Malacria Prof. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2009,15(39):10225-10232
A general and efficient method for the synthesis of cyclic sulfinates and sulfinamides based on intramolecular homolytic substitution (SHi) at the sulfur atom by aryl or alkyl radicals is described. Both alkyl and benzofused compounds can be accessed directly from easily prepared acyclic precursors. Enantiomerically enriched sulfur‐based heterocycles were formed through an SHi process with inversion of configuration at the sulfur atom. Cyclization of prochiral radicals proceeded with varying stereochemical outcomes, depending on the size of the incoming radical. 2‐Pyridyl and 2‐quinolyl radicals led to biaryl compounds, which result from attack onto the ortho position of the arylsulfinate rather than a thiophilic substitution. 相似文献
7.
Sulfonamides have a special role on medicine due to their broad biological activities, as bacterial infections, diabetes mellitus, oedema, hypertension prevention and treatment. In addition, sulfonamides are also useful in herbicides and pesticides. Herein, we communicate an efficient strategy for the preparation of sulfonamides via NH4I‐mediated amination of sodium sulfinates. This new method provides a general and environmentally friendly access to sulfonamide compounds and tolerates a wide range of functional groups. 相似文献
8.
The synthesis and thermal rearrangement of bis-allenyl thiosulfonates are described. Bis-γ,γ-disubstituted allenyl thiosulfonates have been prepared by disproportionation of the corresponding allenesulfinic acids. On heating, these compounds unexpectedly rearrange to a mixture of 1H,3H-thieno[3,4-d][1,2]oxathiine-3-oxide 8, 1H,3H-thieno[3,4-c]thiophene-2,2-dioxide 9, and 3-alkyl-4-alkenylthiophene 10. A tentative reaction mechanism involving sequential sigmatropic rearrangements and cyclizations is suggested. 相似文献
9.
Tianlei Wang Fumin Wang Jinghua Shen Tianting Pang Yanfei Ren Botao Wu Xubin Zhang 《Tetrahedron letters》2018,59(13):1183-1187
A safe and efficient protocol for the synthesis of aryl sulfinates from arenes and 1,4-diazabicyclo[2,2,2]octane bis(sulfur dioxide) (DABSO) under mild conditions is described. Through in situ infrared spectroscopic studies, a plausible mechanism for the sulfination reaction is proposed as well. 相似文献
10.
Jozef Drabowicz James C. Martin 《Phosphorus, sulfur, and silicon and the related elements》2013,188(5-6):1345-1349
Abstract The reaction of 1,1,1,3,3,3-hexafluoro-2-(p-tert-butyl)phenyl-2-propanol with n-butyl-lithium/N,N,N′,N′-tetramethylethylenediamine (TMEDA) provides dilithioderivative 1b, which, upon reaction with thionyl chloride, gave cyclic and acyclic sulfites 3 and 4 as precursors of the sulfurane 2b with simultaneous formation of cyclic sulfinate 5. This ester was utilized for the preparation of asymmetrical spirosulfuranes 7 or ortho-perfluorocumylaryl(alkyl) sulfoxides 8. Attempts to obtain it as an optically active species are also mentioned. 相似文献