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Synthesis
DOI: 10.1055/a-2295-8117
DOI: 10.1055/a-2295-8117
paper
Special Issue PSRC-10 (10th Pacific Symposium on Radical Chemistry)
Boosting Sulfonylation Reactions between Vinyl Triflates and Alkenes toward β-Ketosulfones Using Aqueous Sulfurous Acid
This work was partly supported by the New Energy and Industrial Technology Development Organization (NEDO) (21502091-0) and by the Japan Society for the Promotion of Science (JSPS) Grant-in-Aid for Scientific Research (C) (22K05116).
Abstract
We successfully synthesized trifluoromethylated β-ketosulfones via the reaction of vinyl triflates with alkenes employing aqueous sulfurous acid as an external source of SO2. The PhSSPh/photoinitiated reaction with vinyl triflates that contain electron-deficient groups or halogens did not show any base-related effects, whereas the radical reaction was impeded in the absence of a base in the case of vinyl triflates generated from phenylacetylenes.
Key words
radicals - trifluoromethylation - sulfonylation - vinyl triflates - β-ketosulfones - sulfurous acidSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2295-8117.
- Supporting Information
Publication History
Received: 31 January 2024
Accepted after revision: 27 March 2024
Accepted Manuscript online:
27 March 2024
Article published online:
25 April 2024
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References
- 1 Inoue M, Sumii Y, Shibata N. ACS Omega 2020; 5: 10633
- 2 Ogawa Y, Tokunaga E, Kobayashi O, Hirai K, Shibata N. iScience 2020; 23: 101467
- 3 Nair AS, Singh AK, Kumar A, Kumar S, Sukumaran S, Koyiparambath VP, Pappachen LK, Rangarajan TM, Kim H, Mathew B. Processes 2022; 10: 2054
- 4 Koike T. Asian J. Org. Chem. 2020; 9: 529
- 5 Xiao H, Zhang Z, Fang Y, Zhu L, Li C. Chem. Soc. Rev. 2021; 50: 6308
- 6 Kawamoto T, Sasaki R, Kamimura A. Angew. Chem. Int. Ed. 2017; 56: 1342
- 7 Kawamoto T, Sasaki R, Kamimura A, Matsubara H. J. Fluorine Chem. 2019; 221: 66
- 8 Kawamoto T, Noguchi K, Takata R, Sasaki R, Matsubara H, Kamimura A. Chem. Eur. J. 2021; 27: 9529
- 9 Kawamoto T, Kawabata T, Noguchi K, Kamimura A. Org. Lett. 2022; 24: 324
- 10 Kawamoto T, Kamimura A. Synthesis 2022; 54: 2539
- 11 Su X, Huang H, Yuan Y, Li Y. Angew. Chem. Int. Ed. 2017; 56: 1338
- 12 Liu S, Jie J, Yu J, Yang X. Adv. Synth. Catal. 2018; 360: 267
- 13 Wang H, Bellotti P, Zhang X, Paulisch TO, Glorius F. Chem 2021; 7: 3412
- 14 Shyshkina OO, Popov KS, Gordivska OO, Tkachuk TM, Kovalenko NV, Volovnenko TA, Volovenko YuM. Chem. Heterocycl. Compd. 2011; 47: 923
- 15 Markitanov YM, Timoshenko VM, Shermolovich YG. J. Sulfur Chem. 2014; 35: 188
- 16 Jannapu Reddy R, Haritha Kumari A, Kumar JJ. Org. Biomol. Chem. 2021; 19: 3087
- 17 Kawamoto T, Morioka T, Noguchi K, Curran DP, Kamimura A. Org. Lett. 2021; 23: 1825
- 18 Gerusz V, Denis A, Faivre F, Bonvin Y, Oxoby M, Briet S, LeFralliec G, Oliveira C, Desroy N, Raymond C, Peltier L, Moreau F, Escaich S, Vongsouthi V, Floquet S, Drocourt E, Walton A, Prouvensier L, Saccomani M, Durant L, Genevard J.-M, Sam-Sambo V, Soulama-Mouze C. J. Med. Chem. 2012; 55: 9914
- 19 Hansch C, Leo A, Taft RW. Chem. Rev. 1991; 91: 165
- 20 See the Supporting Information for details.
- 21 Roberts BP. Chem. Soc. Rev. 1999; 28: 25
- 22 Takahara Y, Iino M, Matsuda M. Bull. Chem. Soc. Jpn. 1976; 49: 2268
- 23 Although we used PhSSPh (10 mol%), only trace amounts of 6 were obtained in all reactions. We also observed a dimerization product (1,4-diketones) in around 10% yield based on alkenes. The 1,4-diketone would be formed from vinyl triflate and compound 6.
- 24 Kawamoto T, Ikeda S, Kamimura A. J. Org. Chem. 2021; 86: 13783