1212-08-4Relevant articles and documents
Electrochemical oxidative cyclization of activated alkynes with diselenides or disulfides: Access to functionalized coumarins or quinolinones
Hua, Jiawei,Fang, Zheng,Xu, Jia,Bian, Mixue,Liu, ChengKou,He, Wei,Zhu, Ning,Yang, Zhao,Guo, Kai
, p. 4706 - 4711 (2019)
A direct electrochemical oxidative cyclization of alkynoates and alkynamides with diselenides or disulfides for the synthesis of coumarins and quinolinones bearing a chalcogen functional group has been developed. This green and efficient approach was realized through a constant current electrolysis in an undivided cell under metal-free and oxidant-free conditions. Moreover, a series of selenium/sulfur-substituted coumarin and quinolinone products were obtained in moderate to good yields with a broad scope and functional group tolerance.
A Facile Diastereoselective Synthesis of Functionalized 1,2,3-Trisubstituted Benzocyclopentenes through the Cycloaddition of Bis(phenylsulfonyl)iodonium Ylides to Cyclic Alkenes
Adam, Waldemar,Gogonas, Efstathios P.,Hadjiarapoglou, Lazaros P.
, p. 9155 - 9158 (2003)
The thermal cycloaddition of β-disulfonyl iodonium ylides to cyclic alkenes affords exclusively 1,2,3-trisubstituted cis(1,2)/cis(2,3)-configured benzocyclopentenes by an electrophilic attack of the ylide on the olefinic double bond. This unsual transformation provides a convenient and direct method for the diastereoselective synthesis of functionalized bicyclo [3.3.0] octanes (characteristic structural units contained in polyquinane natural products), when cyclopentenes are used as cycloalkene partner.
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Barnard
, p. 4673 (1957)
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Edmondson et al.
, p. 618 (1971)
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Oxidation of organic sulfides and disulfides with a tert-butyl hydroperoxide-aluminum tri-tert-butoxide system
Zaburdaeva,Dodonov
, p. 185 - 187 (2011)
Methyl phenylethynyl and phenyl phenylethynyl sulfides are selectively converted into methyl phenylethynyl and phenyl phenylethynyl sulfones, respectively, under the action of system tert-butyl hydroperoxide-aluminum tri-tert-butoxide in benzene at 20 °C. The analogous oxidation of diphenyl disulfide results in S-phenyl benzenethiosulfonate.
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Ju,T.-L. et al.
, p. 610 - 614 (1979)
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Metal-free oxidation of sulfides by carbon nitride with visible light illumination at room temperature
Zhang, Pengfei,Wang, Yong,Li, Haoran,Antonietti, Markus
, p. 1904 - 1908 (2012)
Mesoporous graphitic carbon nitride (mpg-C3N4) has been developed as a non-metal, heterogeneous photocatalyst for the selective oxidation of sulfides to sulfoxides with O2 at room temperature. Especially, the combination of mpg-C3N4 and aldehydes was a highly active system under visible-light irradiation. For example, mpg-C 3N4/isobutyraldehyde catalytic oxidation of methyl phenyl sulfide afforded 97% conversion with 98% selectivity for the methyl phenyl sulfoxide in 4 h. Moreover, the mpg-C3N4 can be easily recovered by filtration and then reused at least four times without losing activity. By exploring the electron spin resonance and some comparative experiments, a catalytic mechanism of this oxidation was provided. Finally, the system also works well in the oxidation of a number of sulfides, including sulfides bearing various groups, and phenyl disulfide. The use of a metal-free heterogeneous catalyst and visible light energy, along with the mild reaction conditions makes this oxidation reaction an environmentally benign and energy-saving chemical process. The Royal Society of Chemistry 2012.
Scalable Synthesis of S-Fluoromethyl Benzenesulfonothioate
Chen, Wenbo,Lu, Long,Shen, Qilong,Yao, Ruichao,Zhao, Qunchao
, p. 1090 - 1094 (2020)
A general and practical method for the preparation of S-fluoromethyl benzenesulfonothioate on a 500 g scale in two steps from readily available CH2FCl, sulfur, and sodium benzenesulfinate is reported. The reaction was found to be rather sensitive to water and temperature. Furthermore, the main side product of the reaction was identified to be S-phenyl benzenesulfonothioate.
Chemichal Ionization and Electron Impact Mass Spectra of Thiosulfinates, Thiosulfonates, and Sulfinyl Sulfones
Freeman, Fillmore,Angeletakis, Christos N.
, p. 114 - 122 (1982)
The chemical ionization and electron impact mass spectra of some thiosulfinates, thiosulfonates, and sulfinyl sulfones have been studied.The electron impact mass spectra of four of the six thiosulfonates show molecular ions of less than 1percent.Inconclusive evidence was obtained for sulfenyl sulfinate type intermediates in the electron impact spectra of thiosulfonates.The electron impact spectra of thiosulfonates were similar to those of thiosulfonates.The chemical ionization (isobutane) mass spectra of thiosulfinates and thiosulfonatesgenerally show protonated molecular ions (+) as base peaks and (+) and (+) peaks.
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Abe,Tsurugi
, p. 441 (1972)
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A new synthesis of thioesters and selenoesters of triflic acid under oxidative conditions
Billard, Thierry,Langlois, Bernard R.
, p. 63 - 64 (1997)
Trifluoromethanethio-(or seleno-)sulfonates (CF3SO2YR, Y=S, Se) are easily obtained in one step at 0-20 °C from disulfides (or diselenides), sodium trifluoromethanesulfinate and [bis-(trifluoroacetoxy)iodo]benzene (BTIB).
Enantioselective Nickel-Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution
Liu, En-Chih,Topczewski, Joseph J.
supporting information, p. 5308 - 5313 (2021/05/04)
The triazole heterocycle has been widely adopted as an isostere for the amide bond. Many native amides are α-chiral, being derived from amino acids. This makes α-N-chiral triazoles attractive building blocks. This report describes the first enantioselective triazole synthesis that proceeds via nickel-catalyzed alkyne-azide cycloaddition (NiAAC). This dynamic kinetic resolution is enabled by a spontaneous [3,3]-sigmatropic rearrangement of the allylic azide. The 1,4,5-trisubstituted triazole products, derived from internal alkynes, are complementary to those commonly obtained by the related CuAAC reaction. Initial mechanistic experiments indicate that the NiAAC reaction proceeds through a monometallic Ni complex, which is distinct from the CuAAC manifold.
Visible-Light-Induced Radical Cascade Reaction of 1-Allyl-2-ethynylbenzoimidazoles with Thiosulfonates to Assemble Thiosulfonylated Pyrrolo[1,2-a]benzimidazoles
Liu, Yan,Zhang, Niuniu,Xu, Yanli,Chen, Yanyan
, p. 16882 - 16891 (2021/11/18)
A visible-light-induced radical domino reaction of 1-allyl-2-ethynylbenzoimidazoles with thiosulfonates was developed, which generated the thiosulfonylated pyrrolo[1,2-a]benzimidazoles in moderate to good yields. This reaction proceeded under transition-metal-free conditions with good functional group tolerance and high regioselectivity. The possible pathway involved thiosulfonates were activated through the energy transfer route promoted by photocatalysis.
