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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Ultrasound Accelerated Expedient and Eco-Friendly Synthesis of Aryl Sulfonates Using I2 As Catalyst At Ambient Conditions

Author(s): Sha Zhu, Bin-Bin Wang, Mei-Chen Tan, Xiaofu Qian, Shengneng Ying, Yang Liu, Cehua Li, Zheng Jin, Hongmei Jiang and Qing-Wen Gui*

Volume 19, Issue 4, 2022

Published on: 18 January, 2022

Page: [293 - 297] Pages: 5

DOI: 10.2174/1570178618666210929124259

Price: $65

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Abstract

Aryl sulfonates were developed by ssing an energy-saving and eco-friendly approach, through ultrasound-assisted coupling reaction of readily sodium sulfinates with N-hydroxyphthalimide, under metal-free and mild conditions within 10 min at room temperature.

Keywords: Aryl sulfonates, ultrasound, eco-friendly, iodine, S-O bond forming, radical reactions.

Graphical Abstract

[1]
(a) Tamura, Y.; Ikeda, H.; Morita, I.; Tsubouchi, H.; Ikeda, M. Chem. Pharm. Bull. (Tokyo), 1982, 30, 1221.
[http://dx.doi.org/10.1248/cpb.30.1221]
(b) Paudyal, M.P.; Adebesin, A.M.; Burt, S.R.; Ess, D.H.; Ma, Z.; Kürti, L.; Falck, J.R. Science, 2016, 353(6304), 1144-1147.
[http://dx.doi.org/10.1126/science.aaf8713] [PMID: 27609890]
(c) Cecere, G.; König, C.M.; Alleva, J.L.; MacMillan, D.W. J. Am. Chem. Soc., 2013, 135(31), 11521-11524.
[http://dx.doi.org/10.1021/ja406181e] [PMID: 23869694]
(d) Yang, C.; Liu, Y.; Yang, J.D.; Li, Y.H.; Li, X.; Cheng, J.P. Org. Lett., 2016, 18(5), 1036-1039.
[http://dx.doi.org/10.1021/acs.orglett.6b00163] [PMID: 26911719]
(e) Shen, X.; Harms, K.; Marsch, M.; Meggers, E. Chemistry, 2016, 22(27), 9102-9105.
[http://dx.doi.org/10.1002/chem.201601572] [PMID: 27145893]
(f) Ma, X.; Farndon, J.J.; Young, T.A.; Fey, N.; Bower, J.F. Angew. Chem. Int. Ed., 2017, 56, 14531.
[http://dx.doi.org/10.1002/anie.201708176]
(g) Ortiz, G.X., Jr; Hemric, B.N.; Wang, Q. Org. Lett., 2017, 19(6), 1314-1317.
[http://dx.doi.org/10.1021/acs.orglett.7b00358] [PMID: 28281340]
(h) Zhang, Y.; Du, Y.; Huang, Z.; Xu, J.; Wu, X.; Wang, Y.; Wang, M.; Yang, S.; Webster, R.D.; Chi, Y.R. J. Am. Chem. Soc., 2015, 137(7), 2416-2419.
[http://dx.doi.org/10.1021/ja511371a] [PMID: 25651161]
[2]
(a) Groutas, W.C.; Huang, H.; Epp, J.B.; Brubaker, M.J.; Keller, C.K.; McClenahan, J.J. Bioorg. Med. Chem. Lett., 1992, 2, 1565.
[http://dx.doi.org/10.1016/S0960-894X(00)80431-X]
(b) Abell, A.D.; Oldham, M.D. Bioorg. Med. Chem. Lett., 1999, 9(3), 497-500.
[http://dx.doi.org/10.1016/S0960-894X(99)00017-7] [PMID: 10091709]
(c) Stefanowicz, P.; Jaremko, Ł.; Jaremko, M.; Lis, T. New J. Chem., 2006, 30, 258.
[http://dx.doi.org/10.1039/B513741A]
[3]
(a) Das, B.; Reddy, S.; Reddy, M.R. Tetrahedron Lett., 2004, 45, 6717.
[http://dx.doi.org/10.1016/j.tetlet.2004.07.076]
(b) Das, B.; Reddy, V.S. Chem. Lett., 2004, 33, 1428.
[http://dx.doi.org/10.1246/cl.2004.1428]
(c) Choudary, B.M.; Chowdari, N.S.; Kantam, M.L. Tetrahedron, 2000, 56, 7291.
[http://dx.doi.org/10.1016/S0040-4020(00)00626-8]
(d) Velusamy, S.; Kumar, J.S.K.; Punniyamurthy, T. Tetrahedron Lett., 2004, 45, 203.
[http://dx.doi.org/10.1016/j.tetlet.2003.10.106]
(e) Jalalian, N.; Petersen, T.B.; Olofsson, B. Chemistry, 2012, 18(44), 14140-14149.
[http://dx.doi.org/10.1002/chem.201201645] [PMID: 23015511]
[4]
(a) Melone, L.; Beilstein, C.P. J. Org. Chem., 2013, 9, 1296.
(b) Recupero, F.; Punta, C. Chem. Rev., 2007, 107, 3800.
(c) Ishii, Y.; Sakaguchi, S.; Iwahama, T. Adv. Synth. Catal., 2001, 343, 393.
[5]
(a) Lv, Y.; Sun, K.; Pu, W.; Mao, S.; Li, G.; Niu, J.; Chen, Q.; Wang, T. RSC Advances, 2016, 6, 93486.
[http://dx.doi.org/10.1039/C6RA22653A]
(b) Lv, Y.; Wang, X.; Cui, H.; Sun, K.; Pu, W.; Li, G.; Wu, Y.; He, J.; Ren, X. RSC Advances, 2016, 6, 74917.
[http://dx.doi.org/10.1039/C6RA16266E]
(c) Dian, L.; Wang, S.; Zhang-Negrerie, D.; Du, Y. Adv. Synth. Catal., 2015, 357, 3836.
[http://dx.doi.org/10.1002/adsc.201500623]
(d) Zhou, Y.; Chen, J.; Elsayed, A.A.; Zhang, Z.; Bao, Z.; Yang, Q.; Yang, Y.; Ren, Q. Catal. Lett., 2019, 149, 574.
[http://dx.doi.org/10.1007/s10562-018-2640-9]
(e) Lv, Y.; Sun, K.; Wang, T.; Li, G.; Pu, W.; Chai, N.; Shen, H.; Wu, Y. RSC Advances, 2015, 5, 72142.
[http://dx.doi.org/10.1039/C5RA12691F]
(f) Zhang, M-Z.; Luo, N.; Long, R-Y.; Gou, X-T.; Shi, W-B.; He, S-H.; Jiang, Y.; Chen, J-Y.; Chen, T. J. Org. Chem., 2018, 83(4), 2369-2375.
[http://dx.doi.org/10.1021/acs.joc.7b02740] [PMID: 29400062]
[6]
Liu, T.; Zheng, D.; Li, Z. Wu. J. Adv. Synth. Catal., 2017, 359, 2653.
[http://dx.doi.org/10.1002/adsc.201700501]
[7]
Terent’ev, A.O.; Mulina, O.M.; Parshin, V.D.; Kokorekin, V.A.; Nikishin, G.I. Org. Biomol. Chem., 2019, 17(14), 3482-3488.
[http://dx.doi.org/10.1039/C8OB03162B] [PMID: 30724302]
[8]
(a) Wu, C.; Lu, L-H.; Peng, A-Z.; Jia, G-K.; Peng, C.; Cao, Z.; Tang, Z.; He, W-M.; Xu, X. Green Chem., 2018, 20, 3683.
[http://dx.doi.org/10.1039/C8GC00491A]
(b) Pharande, S.G.; Escobosa, A.R.C. Green Chem., 2017, 19, 1259.
[http://dx.doi.org/10.1039/C6GC03324E]
(c) Banerjee, B. Ultrason. Sonochem, 2017, 35(Pt A), 1-4.
[http://dx.doi.org/10.1016/j.ultsonch.2016.09.023] [PMID: 27771266]
(d) Brahmachari, G.; Mandal, M.; Karmakar, I.; Nurjamal, K.; Mandal, B. ACS Sustain. Chem.& Eng., 2019, 7, 6369.
[http://dx.doi.org/10.1021/acssuschemeng.9b00133]
[9]
(a) Jiang, H.; Tang, X.; Liu, S.; Wang, L.; Shen, H.; Yang, J.; Wang, H.; Gui, Q-W. Org. Biomol. Chem., 2019, 17(48), 10223-10227.
[http://dx.doi.org/10.1039/C9OB02245G] [PMID: 31777898]
(b) Jiang, H.; Guo, D.; Zhang, Y.; Shen, Q.; Tang, S.; You, J.; Huo, Y.; Wang, H.; Gui, Q-W. Synthesis, 2020, 52, 2713.
(c) Gui, Q-W.; Teng, F.; Sheng, S-N.; Liu, Y.; Guo, T.; Tang, J-X.; Chen, J-Y.; Cao, Z.; He, W-M. Chin. Chem. Lett., 2020, 31, 3241.
[http://dx.doi.org/10.1016/j.cclet.2020.07.017]
[10]
Cravotto, G.; Cintas, P. Chem. Soc. Rev., 2006, 35(2), 180-196.
[http://dx.doi.org/10.1039/B503848K] [PMID: 16444299]
[11]
(a) Paveliev, S.A.; Churakov, A.I.; Alimkhanova, L.S.; Segida, O.O. NikiShin, G.I.; Terent’ev, A.O. Adv. Synth. Catal., 2020, 362, 3864.
[http://dx.doi.org/10.1002/adsc.202000618]
(b) Krylov, I.B.; Lopat’eva, E.R.; Budnikov, A.S. NikiShin, G.I.; Terent’ev, A.O. J. Org. Chem., 2020, 85, 1935.
[http://dx.doi.org/10.1021/acs.joc.9b02656] [PMID: 31886660]
(c) Krylov, I.B.; Paveliev, S.A.; Matveeva, O.K.; Terent’ev, A.O. Tetrahedron, 2019, 75, 2529.
[http://dx.doi.org/10.1016/j.tet.2019.03.030]
(d) Krylov, I.B.; Paveliev, S.A.; Shelimov, B.N.; Lokshin, B.V.; Garuzova, I.A.; Tafeenko, V.A.; Chernyshev, V.V.; Budnikov, A.S. NikiShin, G.I.; Terent’ev, A.O. Org. Chem. Front., 2017, 4, 1947.
[http://dx.doi.org/10.1039/C7QO00447H]
(e) Bag, R.; Sar, D.; Punniyamurthy, T. Org. Biomol. Chem., 2016, 14(12), 3246-3255.
[http://dx.doi.org/10.1039/C6OB00210B] [PMID: 26923878]
[12]
(a) Li, L-X.; Dong, D-Q.; Hao, S-H.; Wang, Z-L. Tetrahedron Lett., 2018, 59, 1517.
[http://dx.doi.org/10.1016/j.tetlet.2018.03.023]
(b) Tang, Y.; Fan, Y.; Gao, H.; Li, X.; Xu, X. Tetrahedron Lett., 2015, 56, 5616.
[http://dx.doi.org/10.1016/j.tetlet.2015.08.055]
(c) Mulina, O.M.; Pirgach, D.A.; NikiShin, G.I.; Terent’ev, A.O. Eur. J. Org. Chem., 2019, 4179.
[http://dx.doi.org/10.1002/ejoc.201900258]
(d) Lu, F.; Li, J.; Wang, T.; Li, Z.; Jiang, M.; Hu, X.; Pei, H.; Yuan, F.; Lu, L.; Lei, A. Asian J. Org. Chem., 2019, 8, 1838.
[http://dx.doi.org/10.1002/ajoc.201900447]
(e) Terent’ev, A.O.; Mulina, O.M.; Ilovaisky, A.I.; Kokorekin, V.A.; Nikishin, G.I. Mendeleev Commun., 2018, 29, 80.
[http://dx.doi.org/10.1016/j.mencom.2019.01.027]

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