Visible-Light Induced Sulfonylation of Nitroolefins for the Synthesis of Vinyl Sulfones under Photocatalyst Free Conditions

doi:10.6023/cjoc202006025

Abstract

An eco-friendly visible light-induced approach for the synthesis of vinyl sulfones from the reaction of nitroolefins with sulfinic acid under photocatalyst free conditions was developed. Simple operation, mild reaction conditions, broad substrate scope and good yields of the desired products made this transformation have an excellent prospect. The anti-microbial activity test showed that some of the desired products had moderate inhibitory rate against V. mali and C. glecosporioides.

Key words: visible light, vinyl sulfones, nitroolefins, sulfinic acid

Cite this article

Chen Demao, Sun Yuanyuan, Dong Daoqing, Han Qingqing, Wang Zuli. Visible-Light Induced Sulfonylation of Nitroolefins for the Synthesis of Vinyl Sulfones under Photocatalyst Free Conditions[J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4267-4273.

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References

[1] (a) Fung, E.; Chua, K.; Ganz, T.; Nemeth, E.; Ruchala, P. Bioorg. Med. Chem. Lett. 2015, 25, 763.
(b) Lavecchia, A.; Di Giovanni, C.; Pesapane, A.; Montuori, N.; Ragno, P.; Martucci, N. M.; Masullo, M.; De Vendittis, E.; Novellino, E. J. Med. Chem. 2012, 55, 4142.
(c) Nakao, Y.; Fusetani, N. J. Nat. Prod. 2007, 70, 689.
(d) Goudou, F.; Petit, P.; Moriou, C.; Gros, O.; Al-Mourabit, A. J. Nat. Prod. 2017, 80, 1693.
(e) Gordon, C. P.; Griffith, R.; Keller, P. A. Med. Chem. 2007, 3, 199.
(f) Meadows, D. C.; Sanchez, T.; Neamati, N.; North, T. W.; Hague, J. G. Bioorg. Med. Chem. 2007, 15, 1127.
[2] (a) Simpkins, N. S. Tetrahedron 1990, 46, 6951.
(b) Chen, G.-Y.; Lu, Y. Synthesis 2013, 45, 1654.
(c) Cheng, F.; Wang, H.; He, W.; Sun, B.; Zhao, J.; Qu, J.; Wang, Q. ACS Sustainable Chem. Eng. 2019, 7, 9112.
[3] (a) Truce, W. E.; Goralski, C. T. J. Org. Chem. 1971, 36, 2536.
(b) Posner, G. H.; Brunelle, D. J. J. Org. Chem. 1972, 37, 3547.
(c) Hoogenboom, B. E.; ElFaghi, M. S.; Fink, S. C.; Ihrig, P. I.; Langsjoen, A. N.; Linn, C. J.; Maehling, K. L. J. Org. Chem. 1975, 40, 880.
(d) Back, T. G.; Collins, S.; Krishna, M. V.; Law, K. W. J. Org. Chem. 1987, 52, 4258.
(e) Kamigata, N.; Sawada, H.; Kobayashi, M. J. Org. Chem. 1983, 48, 3793.
(f) Huang, X.; Duan, D.; Zheng, W. J. Org. Chem. 2003, 69, 1958.
(g) Guan, Z. H.; Zuo, W.; Zhao, L. B.; Ren, Z. H.; Liang, Y. M. Synthesis 2007, 1465.
(h) Ochiai, M.; Kitagawa, Y.; Toyonari, M.; Uemura, K.; Oshima, K.; Shiro, M. J. Org. Chem. 1997, 62, 8001.
(i) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Parisi, L. M.; Bernini, R. J. Org. Chem. 2004, 69, 5608.
(j) Battace, A.; Zair, T.; Doucet, H.; Santelli, M. Synthesis 2006, 3495.
(k) Bian, M.; Xu, F.; Ma, C. Synthesis 2007, 2951.
(l) Truce, W.; Wolf, G. C. J. Org. Chem. 1971, 36, 1727.
(m) Amiel, Y. J. Org. Chem. 1970, 36, 3691.
(n) Peng, L.; Hu, Z.; Tang, Z.; Jiao, Y.; Xu, X. Chin. Chem. Lett. 2019, 30, 1481.
(o) Keshari, T.; Kapoorr, R.; Yadav, L. D. S. Eur. J. Org. Chem. 2016, 2695.
[4] (a) Nair, V.; Augustine, A.; George, T. G.; Nair, L. G. Tetrahedron Lett. 2001, 42, 6763.
(b) Katrun, P.; Chiampanichayakul, S.; Korworapan, K.; Pohmakotr, M.; Reutrakul, V.; Jaipetch, T.; Kuhakarn, C. Eur. J. Org. Chem. 2010, 2010, 5633.
(c) Kamigata, N.; Sawada, H.; Kobayashi, M. J. Org. Chem. 1983, 48, 3793.
(d) Taniguchi, N. Synlett 2011, 1308.
(e) Nair, V.; Augustine, A.; Suja, T. D. Synthesis 2002, 2259.
(f) Das, B.; Lingaiah, M.; Damodar, K.; Bhunia, N. Synthesis 2011, 2941.
(g) Sawangphon, T.; Katrun, P.; Chaisiwamongkhol, K.; Pohmakotr, M.; Reutrakul, V.; Jaipetch, T.; Soorukram, D.; Kuhakarn, C. Synth. Commun. 2013, 43, 1692.
(h) Tang, S.; Wu, Y.; Liao, W.; Bai, R.; Liu, C.; Lei, A. Chem. Commun. 2014, 50, 4496.
(i) Zhang, N.; Yang, D.; Wei, W.; Yuan, L.; Cao, Y.; Wang, H. RSC Adv. 2015, 5, 37013.
(j) Luo, Y. C.; Pan, X. J.; Yuan, G. Q. Tetrahedron 2015, 71, 2119.
(k) Xue, Q.; Mao, Z.; Shi, Y.; Mao, H.; Cheng, Y.; Zhu, C. Tetrahedron Lett. 2012, 53, 1851.
(l) Chawla, R.; Kapoor, R.; Singh, A. K.; Yadav, L. D. S. Green Chem. 2012, 14, 1308.
(m) Liang, S.; Zhang, R. Y.; Wang, G.; Chen, S. Y.; Yu, X. Q. Eur. J. Org. Chem. 2013, 2013, 7050.
(n) Katrun, P.; Hlekhlai, S.; Meesin, J.; Pohmakotr, M.; Reutrakul, V.; Jaipetch, T.; Soorukrama, D.; Kuhakarn, C. Org. Biomol. Chem. 2015, 13, 4785
(o) Taniguchi, N. Tetrahedron 2014, 70, 1984.
[5] Nie, G.; Deng, X. C.; Lei, X.; Hu, Q. Q.; Chen, Y. F. RSC Adv. 2016, 6, 75277.
[6] Zhan, Z. Z.; Ma, H. J.; Wei, D. D.; Pu, J. H.; Zhang, Y. X.; Huang, G. S. Tetrahedron Lett. 2018, 59, 1446.
[7] Zhao, Y.; Lai, Y. L.; Du, K. S.; Lin, D. Z.; Huang, J. M. J. Org. Chem. 2017, 82, 9655.
[8] Rong, G. W.; Mao, J. C.; Yan, H.; Zheng, Y.; Zhang, G. Q. J. Org. Chem. 2015, 80, 4697.
[9] Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77.
[10] (a) Chen, Y. Y.; Lu, L. Q.; Yu, D. G.; Zhu, C. J.; Xiao, W. J. Sci. China Chem. 2019, 62, 24-57.
(b) Luo, K.; Yang, W. C.; Wu, L. Asian J. Org. Chem. 2017, 6, 350.
(c) Huang, C.; Li, X. B.; Tung, C. H.; Wu, L. Z. Chem.-Eur. J. 2018, 24, 11530.
(d) Chen, Y.; Zhao, H.; Cheng, D.; Li X.; Xu X. Chin. J. Org. Chem. 2020, 40, 1297(in Chinese). (陈跃峰, 赵赫, 程冬萍, 李小年, 许孝良, 有机化学, 2020, 40, 1297.)
(e) Capaldo, L.; Ravelli, D. Eur. J. Org. Chem. 2017, 2056.
(f) Chen, J. R.; Yan, D. M.; Wei, Q.; Xiao, W. J. ChemPhotoChem 2017, 1, 148.
(g) Peng, S.; Lin, Y.; He, W. Chin. J. Org. Chem. 2020, 40, 541(in Chinese). (彭莎, 林英武, 何卫民, 有机化学, 2020, 40, 541.)
(h) Chen, L.; Liang, J.; Chen, Z. Y.; Chen, J.; Yan, M.; Zhang, X. J. Adv. Synth. Catal. 2019, 361, 956.
(i) Dong, D. Q.; Li, L. X.; Li, G. H.; Deng, Q.; Wang, Z. L.; Long, S. Chin. J. Catal. 2019, 40, 1494.
(j) Kong, Y.; Xu, W.; Ye, F.; Weng, J. Chin. J. Org. Chem. 2019, 39, 3065(in Chinese). (孔瑶蕾, 徐雯秀, 叶飞霞, 翁建全, 有机化学, 2019, 39, 3065.)
(k) Xiao, L.; Li, J.; Wang, T. Acta Chim. Sinica 2019, 77, 841.
(l) Chen, Y.; Chang, L.; Zuo, Z. Acta Chim. Sinica 2019, 77, 794.
(m) Yuan, Y.; Dong, W. H.; Gao, X. S.; Xie, X. M.; Curran, D. P.; Zhang, Z. G. Chin. J. Chem. 2018, 36, 1035.
(o) Wang, D. H.; Zhang, L.; Luo, S. Z. Chin. J. Chem. 2018, 36, 311.
[11] (a) Zhu, J.; Yang, W. C.; Wang, X. D.; Wu, L. Adv. Synth. Catal. 2018, 360, 386.
(b) Li, Y.; Miao, T.; Li, P. H.; Wang, L. Org. Lett. 2018, 20, 1735.
(c) Xie, L. Y.; Fang, T. G.; Tan, J. X.; Zhang, B.; Cao, Z.; Yang, L. H.; He, W. M. Green Chem. 2019, 21, 3858.
(d) Dong, D. Q.; Hao, S. H.; Yang, D. S.; Li, L. X.; Wang, Z. L. Eur. J. Org. Chem. 2017, 2017, 6576.
(e) Li, G.; Gan, Z.; Kong, K.; Dou, X.; Yang, D. Adv. Synth. Catal. 2019, 361, 1808.
(f) Qiu, G. Y. S.; Li, Y. W.; Wu, J. Org. Chem. Front. 2016, 3, 1011.
(g) Lima, C. G. S.; Lima, T. D. M.; Duarte, M.; Jurberg, I. D.; Paixão, M. W. ACS Catal. 2016, 6, 1389.
(h) Duan, K.; Yan, X. F.; Liu, Y. J.; Li, Z. D. Adv. Synth. Catal. 2018, 360, 2781.
(i) Xie, L. Y.; Chen, Y. L.; Qin, L.; Wen, Y.; Xie, J. W.; Tan, J. X.; Huang, Y.; Cao, Z.; He, W. M. Org. Chem. Front. 2019, 6, 3950.
[12] Guo, W.; Tao, K. L.; Tan, W.; Zhao, M. M.; Zheng, L. Y.; Fan, X. L. Org. Chem. Front. 2019, 6, 2048.
[13] Zhu, X. J.; Xie, X. Y.; Li, P. H.; Guo, J. Q.; Wang, L. Org. Lett. 2016, 18, 1546.
[14] Yang, D.; Huang, B.; Wei, W.; Li, J.; Lin, G.; Liu, Y.; Ding, J.; Sun, P.; Wang, H. Green Chem. 2016, 18, 5630.
[15] Meyer, A. U.; Jäger, S.; Hari, D. P.; König, B. Adv. Synth. Catal. 2015, 357, 2050.
[16] Liu, X.; Cong, T.; Liu, P.; Sun, P. Org. Biomol. Chem. 2016, 14, 9416.
[17] (a) Cai, S.; Xu, Y.; Chen, D.; Li, L.; Chen, Q.; Huang, M.; Weng, W. Org. Lett. 2016, 18, 2990.
(b) Dong, D. Q.; Chen, D. M.; Sun, Y. Y.; Han, Q. Q.; Wang, Z. L.; Xu, X. M.; Yu, X. Y. Chin. J. Org. Chem. 2020, 40, 1766(in Chinese). (董道青, 李光辉, 陈德茂, 孙媛媛, 韩晴晴, 王祖利, 徐鑫明, 于贤勇, 有机化学, 2020, 40, 1766.)
(c) Yan, S.; Dong, D. Q.; Xie, C.; Wang, W.; Wang, Z. L. Chin. J. Org. Chem. 2019, 39, 2560.
(d) Li, G. H.; Han, Q. Q.; Sun, Y. Y.; Chen, D. M.; Wang, Z. L.; Xu, X. M.; Yu, X. Y. Chin. Chem. Lett., 2020, 31, 3255.
(e) Li, G. H.; Dong, D. Q.; Deng, Q.; Yan, S. Q.; Wang, Z. L. Synthesis 2019, 51, 3313.
(f) Dong, D. Q.; Chen, W. J.; Yang, Y.; Gao, X.; Wang, Z. L. ChemistrySelect 2019, 4, 2480.
(g) Li, G. H.; Dong, D. Q.; Yu, X. Y.; Wang, Z. L. New J. Chem. 2019, 43, 1667.
(h) Li, G. H.; Dong, D. Q.; Yang, Y.; Yu, X. Y.; Wang, Z. L. Adv. Synth. Catal. 2019, 361, 832.
(i) Dong, D.; Sun, Y.; Li, G.; Yang, H.; Wang, Z.; Xu, X. Chin. J. Org. Chem. 2020, 40, 4071(in Chinese). (董道青, 孙媛媛, 李光辉, 杨欢, 王祖利, 徐鑫明, 有机化学, 2020, 40, 4071.)
(j) Han, Q. Q.; Li, G. H.; Sun, Y. Y.; Chen, D. M.; Wang, Z. L.; Yu, X. Y.; Xu, X. M. Tetrahedron Lett. 2020, 61, 151704.
(k) Dong, D. Q.; Yang, H.; Shi, J. L.; Si, W. J.; Wang, Z. L.; Xu, X. M. Org. Chem. Front. 2020, 7, 2538.
[18] Hong, G. F.; Yuan, J. W.; Dong, Z. H.; Xiao, Y. M.; Mao, P.; Qu, L. B., Phosphorus Sulfur 2018, 193, 771.
[19] Gui, Q. W.; Han, K.; Liu, Z. L.; Su, Z. H.; He, X. L.; Jiang, H. M.; Tian, B. F.; Li, Y. Y. Org. Biomol. Chem. 2018, 16, 5748.
[20] Baliah, V.; Seshapathirao, M. J. Org. Chem. 1959, 24, 867.
[21] Chen, H.; Wedi, P.; Meyer, T.; Tavakoli, G.; van Gemmeren, M. Angew. Chem., Int. Ed. 2018, 57, 2497.
[22] Hu, D. Q.; Bai, F. C.; Liu, Y. Y.; Wan, J. P. Chin. J. Chem. 2016, 34, 1053.
[23] Chen, J.; Mao, J. C.; Zheng, Y.; Liu, D. F.; Rong, G. W.; Yan, H.; Zhang, C.; Shi, D. Q. Tetrahedron 2015, 71, 5059.
[24] Mao, S.; Gao, Y. R.; Zhu, X. Q.; Guo, D. D.; Wang, Y. Q. Org. Lett. 2015, 17, 1692.
[25] Aegurla, B.; Peddinti, R. K. Asian J. Org. Chem. 2018, 7, 946.

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