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Journal articles on the topic 'Desulfonylation'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Nájera, Carmen, and Miguel Yus. "Desulfonylation reactions: Recent developments." Tetrahedron 55, no. 35 (1999): 10547–658. http://dx.doi.org/10.1016/s0040-4020(99)00600-6.

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2

Niu, Ben, Ping Xie, Wannian Zhao, et al. "Metal-free syntheses of oxindole derivatives via a benzoylation/substitution/desulfonylation/cyclization cascade." RSC Adv. 4, no. 82 (2014): 43525–28. http://dx.doi.org/10.1039/c4ra06810f.

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3

Liu, Cuibo, та Bin Zhang. "Light-mediated cascade transformation of activated alkenes: BiOBr nanosheets as efficient photocatalysts for the synthesis of α-aryl-β-trifluoromethyl amides". RSC Advances 5, № 75 (2015): 61199–203. http://dx.doi.org/10.1039/c5ra08996d.

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4

Sun, Fang, Tingrui Yin, Yang Wang, et al. "A combined experimental and computational study of NHC-promoted desulfonylation of tosylated aldimines." Organic Chemistry Frontiers 7, no. 3 (2020): 578–83. http://dx.doi.org/10.1039/c9qo01402k.

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NHC-catalyzed mild desulfonylation of tosylated aldimines provides efficient access to aryl nitriles with broad substrate scope. DFT calculations demonstrate that the reaction undergoes multiple stepwise processes.

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5

Jiang, Ying, Wan-Yin Fang, K. P. Rakesh, and Hua-Li Qin. "Copper-catalyzed mild desulfonylation of vinyl sulfonyl molecules." Organic Chemistry Frontiers 7, no. 13 (2020): 1696–702. http://dx.doi.org/10.1039/d0qo00468e.

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6

Satoh, Tetsuya, Kenji Itoh, Masahiro Miura, and Masakatsu Nomura. "Desulfonylation and desulfonylative carbonylation of arenethiosulfonic acid esters in the presence of PdCl2 and LiCl." Journal of Molecular Catalysis 83, no. 1-2 (1993): 125–33. http://dx.doi.org/10.1016/0304-5102(93)87013-x.

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7

Chen, Huangguan, Limin Wang, and Jianwei Han. "Aryl radical-induced desulfonylative ipso-substitution of diaryliodonium salts: an efficient route to sterically hindered biarylamines." Chemical Communications 56, no. 42 (2020): 5697–700. http://dx.doi.org/10.1039/d0cc01766c.

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By using vicinal aryl sulfonamide-substituted diaryliodonium salts, a cascade of desulfonylation/aryl migration was promoted by triethylamine in synthesis of sterically hindered biarylamines, which operated via a radical-induced reaction pathway.

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8

Parsons, Andrew F., and Robert M. Pettifer. "A radical approach to N-desulfonylation." Tetrahedron Letters 37, no. 10 (1996): 1667–70. http://dx.doi.org/10.1016/0040-4039(96)00086-x.

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9

Najera, Carmen, and Miguel Yus. "ChemInform Abstract: Desulfonylation Reactions: Recent Developments." ChemInform 30, no. 46 (2010): no. http://dx.doi.org/10.1002/chin.199946282.

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10

Knowles, Haydn, Andrew Parsons, and Robert Pettifer. "Desulfonylation of Amides Using Samarium Iodide." Synlett 1997, no. 3 (1997): 271–72. http://dx.doi.org/10.1055/s-1997-771.

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11

Kern, Christoph, Jan Selau та Jan Streuff. "A Titanium‐Catalyzed Reductive α‐Desulfonylation". Chemistry – A European Journal 27, № 20 (2021): 6178–82. http://dx.doi.org/10.1002/chem.202005400.

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12

Chandrasekhar, Srivari, Vikram Gaddam, Lavanya Nadella, Genji Sukumar, and Prathama Mainkar. "Stereoselective Synthesis of Northern Fragment of Eribulin Mesylate from d-Mannose." Synthesis 50, no. 09 (2018): 1901–6. http://dx.doi.org/10.1055/s-0036-1591769.

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Stereoselective synthesis of northern fragment of eribulin mesylate is reported by coupling of the C1–C13 fragment with the C28–C35 fragment. The key steps involved in this synthesis are butyllithium-facilitated coupling between sulfone and aldehyde, then Dess–Martin periodinane oxidation followed by samarium(II) iodide mediated desulfonylation.

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13

Rieger, Elisabeth, Tassilo Gleede, Angelika Manhart, Markus Lamla, and Frederik R. Wurm. "Microwave-Assisted Desulfonylation of Polysulfonamides toward Polypropylenimine." ACS Macro Letters 7, no. 6 (2018): 598–603. http://dx.doi.org/10.1021/acsmacrolett.8b00180.

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14

Hadzic, Pavle, and Nada Vukojevic. "Selective desulfonylation in D-xylofuranose 3,5-disulfonates." Journal of the Serbian Chemical Society 66, no. 5 (2001): 289–95. http://dx.doi.org/10.2298/jsc0105289h.

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A method for the preparation of D-xylofuranose derivatives with a free terminal (C5) alcohol function was developed, starting from monocyclohexylidene-3,5-disulfonyl- or 5-O-sulfonyl-3-O-methyl ester. The regioselective displacement of the C5 sulfonyl ester functionwith acetate ion in dimethylsulfoxide afforded the corresponding 5-O-acetyl-1,2-O-cyclohexylidene-3-O-sulfonyl or 5-O-acetyl-3-O-methyl- -D-xylofuranose. These esters could be readily hydrolysed into the desired 1,2,3-trisubstituted xylofuranose.

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15

Bateman, Thomas J., John S. Debenham, Christina Madsen-Duggan, et al. "Glutathione S-Transferase Catalyzed Desulfonylation of a Sulfonylfuropyridine." Drug Metabolism and Disposition 38, no. 1 (2009): 108–14. http://dx.doi.org/10.1124/dmd.109.029801.

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16

PARSONS, A. F., and R. M. PETTIFER. "ChemInform Abstract: A Radical Approach to N-Desulfonylation." ChemInform 27, no. 26 (2010): no. http://dx.doi.org/10.1002/chin.199626105.

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17

KNOWLES, H., A. F. PARSONS, and R. M. PETTIFER. "ChemInform Abstract: Desulfonylation of Amides Using Samarium Iodide." ChemInform 28, no. 40 (2010): no. http://dx.doi.org/10.1002/chin.199740091.

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18

Guo, Hongyun, Suming Ye, Junquan Wang та Yongmin Zhang. "Reductive Desulfonylation of β-Ketosulfones by TiCl4–Zn†". Journal of Chemical Research, № 3 (1997): 114. http://dx.doi.org/10.1039/a606405a.

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19

Liu, Qiang, Bing Han, Zhengang Liu, Li Yang, Zhong-Li Liu та Wei Yu. "Photochemical reductive desulfonylation of β-ketosulfones by ascorbic acid". Tetrahedron Letters 47, № 11 (2006): 1805–7. http://dx.doi.org/10.1016/j.tetlet.2006.01.023.

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20

Huang, Xian, та Han-Zhong Zhang. "Tandem Reduction-Desulfonylation of α-Alkylidene-β-Keto Sulfones". Synthetic Communications 19, № 1-2 (1989): 97–105. http://dx.doi.org/10.1080/00397918908050957.

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21

Yang, Deng-Tao, Qing-Yuan Meng, Jian-Ji Zhong, Ming Xiang, Qiang Liu, and Li-Zhu Wu. "Metal-Free Desulfonylation Reaction Through Visible-Light Photoredox Catalysis." European Journal of Organic Chemistry 2013, no. 33 (2013): 7528–32. http://dx.doi.org/10.1002/ejoc.201301105.

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22

Hyeong Lee, Ge, Eun Bok Choi, Eun Lee, and Chwang Siek Pak. "An efficient desulfonylation method mediated by magnesium in ethanol." Tetrahedron Letters 34, no. 28 (1993): 4541–42. http://dx.doi.org/10.1016/0040-4039(93)88080-3.

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23

Orita, Akihiro, Hikaru Watanabe, Kazuki Nakajima, et al. "Custom-Made Pyrene Photocatalyst-Promoted Desulfonylation of Arylethenyl Sulfones Using Green-Light-Emitting Diodes." Synthesis 53, no. 17 (2021): 2984–94. http://dx.doi.org/10.1055/s-0040-1706025.

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AbstractThe Sonogashira coupling of 1,3,6,8-tetrabromopyrene with 4-[(–)-β-citronellyloxy]phenylethyne was employed to synthesize 1,3,6,8-tetra[4-(citronellyloxy)phenylethynyl]pyrene. The pyrene derivative catalyzed the reductive desulfonylation of ethenyl sulfones via visible-light irradiation (514 nm green light-emitting diodes) in the presence of i-Pr2NEt. The β-citronellyloxy groups provided the sufficient solubility to the highly π-expanded pyrene catalyst, and their polar oxygen functionalities enabled the easy separation of the catalyst from the products via column chromatography.

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24

Curran, DP, and SN Sun. "Tandem Radical Cyclizations: a One-Step Synthesis of Stereoisomeric Tricyclo[6.3.0.02,6]undecanes From Acyclic Precursors." Australian Journal of Chemistry 48, no. 2 (1995): 261. http://dx.doi.org/10.1071/ch9950261.

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Radical cyclization of (1E,5Z)-1-iodoundeca-1,5,10-triene with triphenyltin hydride provides one acyclic, one monocyclic, two bicyclic and four tricyclic products. At low concentration (0.002 M), the title tricycloundecane products resulting from triple cyclization predominate, but the stereoselectivity is low. Cyclization of (1E,5Z)-1-iodo-8,8-bis( phenylsulfonyl )undeca-1,5,10-triene followed by reductive desulfonylation provides a similar ratio of products to the parent. The results show that this class of triple cyclization occurs well, but the level of stereoselectivity must be raised for

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25

Chou, Ta-shue, and Mei-Li You. "Convenient desulfonylation reactions of cyclic sulfones with ultrasonically dispersed potassium." Tetrahedron Letters 26, no. 37 (1985): 4495–98. http://dx.doi.org/10.1016/s0040-4039(00)88939-x.

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26

Wang, Junquan, та Yongmin Zhang. "The Reductive Desulfonylation of β-Ketosulfones with TiCl4/Sm System". Synthetic Communications 26, № 10 (1996): 1931–34. http://dx.doi.org/10.1080/00397919608003547.

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27

Brown, Alan C., and Louis A. Carpino. "Magnesium in methanol: substitute for sodium amalgam in desulfonylation reactions." Journal of Organic Chemistry 50, no. 10 (1985): 1749–50. http://dx.doi.org/10.1021/jo00210a035.

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28

Zhou, Aihua, Ben Niu, Ping Xie, et al. "Synthesis of Nitromethyl-Substituted Oxindole Derivatives via a Desulfonylation Cascade." Synlett 26, no. 05 (2015): 635–38. http://dx.doi.org/10.1055/s-0034-1378947.

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29

Shinoda, Tsutomu, Tohru Nishiwaki, and Haruo Inoue. "Desulfonylation of poly(4-hydroxystyrene sulfone) by vapor phase silylation." Journal of Polymer Science Part A: Polymer Chemistry 37, no. 10 (1999): 1549–54. http://dx.doi.org/10.1002/(sici)1099-0518(19990515)37:10<1549::aid-pola16>3.0.co;2-g.

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30

GUO, H., S. YE, J. WANG та Y. ZHANG. "ChemInform Abstract: Reductive Desulfonylation of β-Ketosulfones by TiCl4-Zn." ChemInform 28, № 27 (2010): no. http://dx.doi.org/10.1002/chin.199727062.

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31

Viaud-Massuard, Marie-Claude, Charlotte Chaulet, Cécile Croix, Joan Basset, and Maria-Dolores Pujol. "Desulfonylation of Indoles and 7-Azaindoles Using Sodium tert-Butoxide." Synlett 2010, no. 10 (2010): 1481–84. http://dx.doi.org/10.1055/s-0029-1219918.

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32

Guijarro, David, and Miguel Yus. "Naphthalene-catalysed reductive desulfonylation with lithium: Alkyllithiums from alkyl phenyl sulfones." Tetrahedron Letters 35, no. 18 (1994): 2965–68. http://dx.doi.org/10.1016/s0040-4039(00)76673-1.

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33

Carretero, Juan C., Nuria Díaz, Ma Luisa Molina, and Javier Rojo. "Unexpected synthesis of 1,6-dioxadecalins by desulfonylation of phenylsulfonyl [4,5] spiroketals." Tetrahedron Letters 37, no. 18 (1996): 3179–82. http://dx.doi.org/10.1016/0040-4039(96)00489-3.

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34

Qiu, Jiang-Kai, Wen-Juan Hao, Li-Fang Kong, Wei Ping, Shu-Jiang Tu, and Bo Jiang. "Metal-free synthesis of sulfonylated amides through radical aryl migration–desulfonylation." Tetrahedron Letters 57, no. 22 (2016): 2414–17. http://dx.doi.org/10.1016/j.tetlet.2016.04.073.

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35

Tang, Shi, Li Yuan, You-Lin Deng, et al. "Visible-light-induced perfluoroalkylation/arylmigration/desulfonylation cascades of conjugated tosyl amides." Tetrahedron Letters 58, no. 4 (2017): 329–32. http://dx.doi.org/10.1016/j.tetlet.2016.12.027.

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36

Ni, Chuanfa, and Jinbo Hu. "Nucleophilic difluoromethylation of carbonyl compounds using TMSCF2SO2Ph and Mg0-mediated desulfonylation." Tetrahedron Letters 46, no. 48 (2005): 8273–77. http://dx.doi.org/10.1016/j.tetlet.2005.09.162.

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37

Mani, R. S., and D. K. Mohanty. "Competing Desulfonylation and SNAR Reactions During Aromatic Poly(Ether-sulfone) Synthesis." Journal of Macromolecular Science, Part A 32, sup8 (1995): 1189–97. http://dx.doi.org/10.1080/10601329508020340.

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38

Park, Kwanghee Koh, Chul Woo Lee та Sook Young Choi. "Viologen-mediated reductive desulfonylation of α-nitro sulfones by sodium dithionite". J. Chem. Soc., Perkin Trans. 1, № 5 (1992): 601–3. http://dx.doi.org/10.1039/p19920000601.

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39

Inanaga, Kazato, Takashi Fukuyama, Manabu Kubota та ін. "Novel and Efficient Chromium(II)-Mediated Desulfonylation of α-Sulfonyl Ketone". Organic Letters 17, № 12 (2015): 3158–61. http://dx.doi.org/10.1021/acs.orglett.5b01497.

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40

Smith, Amos B., Karl J. Hale та John P. McCauley. "An efficient new method for the desulfonylation of β-keto phenylsulfones". Tetrahedron Letters 30, № 41 (1989): 5579–82. http://dx.doi.org/10.1016/s0040-4039(01)93804-3.

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41

LEE, G. H., E. B. CHOI, E. LEE, and C. S. PAK. "ChemInform Abstract: An Efficient Desulfonylation Method Mediated by Magnesium in Ethanol." ChemInform 24, no. 40 (2010): no. http://dx.doi.org/10.1002/chin.199340130.

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42

WANG, J., та Y. ZHANG. "ChemInform Abstract: Reductive Desulfonylation of β-Ketosulfones with TiCl4/Sm System." ChemInform 27, № 34 (2010): no. http://dx.doi.org/10.1002/chin.199634065.

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43

Yang, Deng-Tao, Qing-Yuan Meng, Jian-Ji Zhong, Ming Xiang, Qiang Liu, and Li-Zhu Wu. "ChemInform Abstract: Metal-Free Desulfonylation Reaction Through Visible-Light Photoredox Catalysis." ChemInform 45, no. 18 (2014): no. http://dx.doi.org/10.1002/chin.201418037.

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44

Gleiter, Rolf, and Frank Ohlbach. "In Quest of a Prismene. Organolithium-Induced Desulfonylation on Strained Hydrocarbons." Journal of Organic Chemistry 61, no. 15 (1996): 4929–32. http://dx.doi.org/10.1021/jo960327b.

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45

Künzer, H., M. Stahnke, G. Sauer, and R. Wiechert. "Reductive desulfonylation of phenyl sulfones by samarium(II) iodide-hexamethylphosphoric triamide." Tetrahedron Letters 32, no. 17 (1991): 1949–52. http://dx.doi.org/10.1016/0040-4039(91)85009-t.

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46

Alonso, Emma, David Guijarro, and Miguel Yus. "Arene-catalysed reductive desulfonylation and desulfinylation reactions: New routes for alkyllithiums." Tetrahedron 51, no. 9 (1995): 2699–708. http://dx.doi.org/10.1016/0040-4020(94)01116-h.

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47

Vargas, Didier, Enrique Larghi, and Teodoro Kaufman. "Concise Synthesis of the ABC-Ring System of the Azafluoranthene, Tropoisoquinoline and Proaporphine Alkaloids: An Olefin Hydroacylation/Pomeranz–Fritsch Cyclization Approach." Synthesis 51, no. 09 (2019): 2030–38. http://dx.doi.org/10.1055/s-0037-1611711.

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A straightforward approach toward a decorated cyclopenta[ij]isoquinoline embodying the ABC-ring system characteristic of the azafluoranthene (triclisine), tropoisoquinoline (pareitropone) and proaporphine (prodensiflorin B) alkaloids, is reported. The synthetic sequence entailed a novel 40% KF/Al2O3-mediated hydroacylation of a 2-allyl-benzaldehyde derivative, obtained in two steps from isovanillin, through O-allylation and Claisen rearrangement to assemble the AC-ring system. This was followed by an O-methylation and a reductive amination of the resulting indanone with aminoacetal. A modifi

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48

Yang, Ji-Cheng, Hong-Bo Ni, Jin Li, Cheng-Xue Zhao, and Yong-Ming Zhang. "Synthesis and Characterisation of P-perfluoro{-1-[2-(2-fluorosulfonylethoxy) Propoxy]}Ethylated Polystyrene." Journal of Chemical Research 2005, no. 8 (2005): 546–48. http://dx.doi.org/10.3184/030823405774663336.

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A new kind of fluorinated polystyrene bearing a p-perfluoro{-1-[2-(2-fluorosulfonyl)propoxy]}ethyl group has been synthesised by one-electron oxidation of polystyrene by perfluoro{2-[2-(2-fluorosulfonyl) propoxy]}propionyl peroxide at different peroxide to polystyrene molar ratios. The yield of ω–fluorosulfonyl perfluoroalkylation decreases with increase in the reactant molar ratio. The modified polymer was characterised by various techniques: the ring perfluoro{-1-[2-(2-fluorosulfonyl)propoxy]}ethylation was proved by FT-IR, 19F NMR and DSC; desulfonylation of the fluorinated polystyrene appe

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49

King, James Frederick, and Kishan Chand Khemani. "Synthesis and thermolysis of 2-(phenylthio)ethanesulfonyl chloride. The absence of a reported "rearrangement of radicals with migration of the chlorine atom from sulfur to carbon"." Canadian Journal of Chemistry 63, no. 3 (1985): 619–22. http://dx.doi.org/10.1139/v85-101.

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2-(Phenylthio)ethanesulfonyl chloride (1) is the major product of the reaction of (a) lithium 2-(phenylthio)ethanesulfinate (6) and chlorine, and, notwithstanding contrary reports, also of (b) benzenethiol (3) and ethenesulfonyl chloride (4), and (c) sodium 2-(phenylthio)ethanesulfonate (5) and phosphorus pentachloride. The rearrangement referred to in the title, which was proposed to account for the isolation of 2-(phenylthio)ethyl chloride (2) rather than 1 from 3 and 4, therefore does not occur. Desulfonylation of 1 to form 2, however, readily takes place thermally and, in accord with a rat

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50

Gao, Yuzhen, Guozhang Lu, Pengbo Zhang, Liangliang Zhang, Guo Tang, and Yufen Zhao. "A Cascade Phosphinoylation/Cyclization/Desulfonylation Process for the Synthesis of 3-Phosphinoylindoles." Organic Letters 18, no. 6 (2016): 1242–45. http://dx.doi.org/10.1021/acs.orglett.6b00056.

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