Hypervalent Organoiodine Promoted Dearylation Reaction of N-Aryl Sulfonamides

doi:10.6023/cjoc202001007

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (8): 2433-2441.DOI: 10.6023/cjoc202001007 Previous Articles Next Articles

高价碘试剂促进的N-芳基磺酰胺类化合物脱芳基反应

宋蒙蒙^a, 张志国^a, 郑丹^b, 李祥^a, 梁蕊^a, 赵旭娜^a, 时蕾^a, 张贵生^a

a 河南师范大学化学化工学院河南新乡 453007;
b 许昌市质量技术监督检验测试中心河南许昌 461000

收稿日期:2020-01-04 修回日期:2020-05-16 发布日期:2020-05-28
通讯作者: 张志国, 张贵生 E-mail:Zhangzg@htu.edu.cn;zgs6668@yahoo.com
基金资助:
国家自然科学基金（Nos.U1604285，21772032，21702051）、长江学者和创新团队发展计划（No.IRT1061）、工业过程智能控制创新引智基地（No.D17007）和河南省教育厅重点（No.18A150009）资助项目.

Hypervalent Organoiodine Promoted Dearylation Reaction of N-Aryl Sulfonamides

Song Mengmeng^a, Zhang Zhiguo^a, Zheng Dan^b, Li Xiang^a, Liang Rui^a, Zhao Xu'na^a, Shi Lei^a, Zhang Guisheng^a

a School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007;
b Quality and Technique Supervision, Inspection and Testing Center of Xuchang City, Xuchang, Henan 461000

Received:2020-01-04 Revised:2020-05-16 Published:2020-05-28
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. U1604285, 21772032, 21702051), Program for Changjiang Scholars and Innovative Research Team in University (No. IRT1061), Industrial Process Intelligent Control Innovation and Talent Recruitment Base (No. D17007) and the Key Project of Henan Educational Committee (No. 18A150009).

1. cjoc202001007辅助材料.pdf(3291KB)

Abstract

An efficient Dess-Martin periodinane (DMP)-promoted dearylation of N-arylsulfonamides was developed through a highly selective oxidative cleavage of the inert C(aryl)-N bonds in secondary sulfonamides while leaving the S-N bond unchanged. This metal-free reaction proceeds under mild conditions and provides access to various biologically important primary sulfonamides, some of which are otherwise unattainable using conventional aminolysis and hydrolysis methods. The concise and efficient dearylation reaction provides the use of an aryl group as a removable protecting sulfonamide group under metal catalyst-free conditions.

Key words: Dess-Martin periodinane (DMP), C(aryl)-N bond cleavage, oxidation, metal-free reaction, sulfonamide

Cite this article

Song Mengmeng, Zhang Zhiguo, Zheng Dan, Li Xiang, Liang Rui, Zhao Xu'na, Shi Lei, Zhang Guisheng. Hypervalent Organoiodine Promoted Dearylation Reaction of N-Aryl Sulfonamides[J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2433-2441.

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[1] (a) Zhang, F.; Zheng, D.; Lai, L.; Cheng, J.; Sun, J.; Wu, J. Org. Lett. 2018, 20, 1167.
(b) Nematollahi, D.; Davarani, S. S. H.; Mirahmadpour, P.; Varmaghani, F. Chin. Chem. Lett. 2014, 25, 593.
(c) Sun, K.; Shi, Z.; Liu, Z.; Luan, B.; Zhu, J.; Xue, Y. Org. Lett. 2018, 20, 6687.
[2] For a List of Sulfa Drugs, See:http://www.thefullwiki.org/Sulfa_drugs.
[3] (a) Wang, X.; Ahn,Y. M.; Lentscher, A. G.; Lister, J. S.; Brothers, R. C.; Kneen, M. M.; Gerratana, B.; Boshoff, H. I.; Dowd, C. S. Bioorg. Med. Chem. Lett. 2017, 27, 4426.
(b) Ascenzio, M. D.; Guglielmi, P.; Carradori, S.; Secci, D.; Florio, R.; Mollica, A.; Ceruso, M.; Akdemir, A.; Sobolev, A. P.; Supuran, C. T. J. Enzym. Inhib. Med. Chem. 2017, 32, 51.
(c) Luci, D. K.; Jameson, J. B.; Yasgar, A.; Diaz, G.; Joshi, N.; Kantz, A.; Markham, K.; Perry, S.; Kuhn, N.; Yeung, J.; Kerns, E. H.; Schultz, L.; Holinstat, M.; Nadler, J. L.; Taylor-Fishwick, D. A.; Jadhav, A.; Simeonov, A.; Holman, T. R.; Maloney, D. J. J. Med. Chem. 2014, 57, 495.
(d) Walsh, M. J.; Brimacombe, K. R.; Veith, H.; Bougie, J. M.; Daniel, T.; Leister, W.; Cantley, L. C.; Israelsen, W. J.; Vander Heiden, M. G.; Shen, M.; Auld, D. S.; Thomas, C. J.; Boxer, M. B. Bioorg. Med. Chem. Lett. 2011, 21, 6322.
(e) Al-Nadaf, A.; Sheikha, G. A.; Taha, M. O. Bioorg. Med. Chem. 2010, 18, 3088.
(f) Wydysh, E. A.; Medghalchi, S. M.; Vadlamudi, A.; Townsend, C. A. J. Med. Chem. 2009, 52, 3317.
(g) Johnson, S. L.; Chen, L. H.; Barile, E.; Emdadi, A.; Sabet, M.; Yuan, H.; Wei, J.; Guiney, D.; Pellecchia, M. S. Bioorg. Med. Chem. 2009, 17, 3352.
(h) Zheng, X.; Oda, H.; Takamatsu, K.; Sugimoto, Y.; Tai, A.; Akaho, E.; Ali, H. I.; Oshiki, T.; Kakuta, H.; Sasaki, K. Bioorg. Med. Chem. 2007, 15, 1014.
(i) Terrett, N. K.; Bell, A. S.; Brown, D.; Ellis, P. Bioorg. Med. Chem. Lett. 1996, 6, 1819.
[4] (a) Shi, M.; Yang, Y. H.; Xu, B. Synlett 2004, 1622.
(b) Liu, C. R.; Li, M. B.; Cheng, D. J.; Yang, C. F.; Tian, S. K. Org. Lett. 2009, 11, 2543.
(c) Liu, Z.; Larock, R. C. Org. Lett. 2003, 5, 4673.
(d) Fu, W.; Shen, R.; Bai, E.; Zhang, L.; Chen, Q.; Fang, Z.; Li, G.; Yi, X.; Zheng, A.; Tang, T. ACS Catal. 2018, 8, 9043.
(e) Gong, X.; Xia, H.; Wu, J. Org. Chem. Front. 2016, 3, 697.
(f) Yu, J.; Liu, S. S.; Cui, J.; Hou, X. S.; Zhang, C. Org. Lett. 2012, 14, 832.
(g) Xiang, Y.; Kuang, Y.; Wu, J. Org. Chem. Front. 2016, 3, 901.
(h) Li, Y. X.; Li, L. H.; Yang, Y. F.; Hua, H. L.; Yan, X. B.; Zhao, L. B.; Zhang, J. B.; Ji, F. J.; Liang, Y. M. Chem. Commun. 2014, 50, 9936.
(i) Chen, K.; Shi, B. F. Angew. Chem., Int. Ed. 2014, 53, 11950.
(j) Wang, H. Y.; Zhang, X.; Guo, Y. L.; Dong, X. C.; Tang, Q. H.; Lu, L. Rapid Commun. Mass Spectrom. 2005, 19, 1696.
(k) Feng, S. L.; Liu, C. Z.; Li, Q.; Yu, X. C.; Xu, Q. Chin. Chem. Lett. 2011, 22, 1021.
(l) Sun, K.; Li, Y.-L.; Feng, R.-R.; Mu, S.-Q.; Wang, X.; Zhang, B. J. Org. Chem. 2019, 84, 12792.
[5] Yao, B.; Zhang, Y. Tetrahedron Lett. 2008, 49, 5385.
[6] Hewson, A. T.; Sharpe, D. A.; Wadsworth, A. H. Synth. Commun. 1989, 19, 2095.
[7] Wang, S. E.; Wang, L.; He, Q.; Fan, R. Angew. Chem., Int. Ed. 2015, 54, 13655.
[8] Katohgi, M.; Yokoyama, M.; Togo, H. Synlett 2000, 1055.
[9] (a) Wang, Q.; Su, Y.; Li, L.; Huang, H. Chem. Soc. Rev. 2016, 45, 1257.
(b) Taniguchi, T.; Imoto, M.; Takeda, M.; Matsumoto, F.; Nakai, T.; Mihara, M.; Mizuno, T.; Nomoto, A.; Ogawa, A. Tetrahedron 2016, 72, 4132.
(c) Azzena, U.; Cattari, M.; Melloni, G.; Pisano, L. Synthesis 2003, 2811.
(d) Koreeda, T.; Kochi, T.; Kakiuchi, F. J. Organomet. Chem. 2013, 741~742, 148.
(e) Koreeda, T.; Kochi, T.; Kakiuchi, F. Organometallics 2013, 32, 682.
(f) Koreeda, T.; Kochi, T.; Kakiuchi, F. J. Am. Chem. Soc. 2009, 131, 7238.
(g) Ueno, S.; Chatani, N.; Kakiuchi, F. J. Am. Chem. Soc. 2007, 129, 6098.
[10] (a) Kamal, R.; Kumar, V.; Kumar, R. Chem.-Asian. J. 2016, 11, 1988.
(b) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
(c) Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016, 116, 3328.
(d) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
(e) Zhdankin, V. V. ARKIVOC 2009, 1.
(f) Ladziata, U.; Zhdankin, V. V. ARKIVOC 2006, 26.
[11] (a) Wan, Y.; Zhang, Z.; Ma, N.; Bi, J.; Zhang, G. J. Org. Chem. 2018, 84, 780.
(b) Zhang, Z.; Gao, X.; Yu, H.; Zhang, G.; Liu, J. Adv. Synth. Catal. 2018, 360, 3406.
(c) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
(d) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
(e) Zhang, Z.; Zhang, Y.; Huang, G.; Zhang, G. Org. Chem. Front. 2017, 4, 1372.
(f) Zhang, Z.; Gao, X.; Li, Z.; Zhang, G.; Ma, N.; Liu, Q.; Liu, T. Org. Chem. Front. 2017, 4, 404.
(g) Liu, Y.; Zhang, Z.; Wan, Y.; Zhang, G.; Li, Z.; Bi, J.; Ma, N.; Liu, T.; Liu, Q. J. Org. Chem. 2017, 82, 3901.
[12] (a) Onundi, Y.; Drake, B. A.; Malecky, R. T.; DeNardo, M. A.; Mills, M. R.; Kundu, S.; Ryabov, A. D.; Beach, E. S.; Horwitz, C. P.; Simonich, M. T.; Truong, L.; Tanguay, R. L.; Wright, L. J.; Singhal, N.; Collins, T. J. Green Chem. 2017, 19, 4234.
(b) Lu, L. H.; Wang, Z.; Xia, W.; Cheng, P.; Zhang, B.; Cao, Z.; He, W. M. Chin. Chem. Lett. 2019, 30, 1237.
(c) Xie, L. Y.; Duan, Y.; Lu, L. H.; Li, Y. J.; Peng, S.; Wu, C.; Liu, K. J.; Wang, Z.; He, W. M. ACS Sustainable Chem. Eng. 2017, 5, 10407.
[13] Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537.
[14] (a) Zhang, Z.; Zheng, D.; Wan, Y.; Zhang, G.; Bi, J.; Liu, Q.; Liu, T.; Shi, L. J. Org. Chem. 2018, 83, 1369.
(b) Zhang, Z.; Li, X.; Song, M.; Wan, Y.; Zheng, D.; Zhang, G.; Chen, G. J. Org. Chem. 2019. 84, 12792.
[15] Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, John Wiley & Sons Inc., 1999.
[16] Zhang, Y.; Li, Y.; Zhang, X.; Jiang, X. Chem. Commun. 2015, 51, 941.
[17] Debnath, S.; Mondal, S. ChemistrySelect 2018, 3, 4129.
[18] Al-Shawabkeh, J. D.; Al-Nadaf, A. H.; Dahabiyeh, L. A.; Taha, M. O. Med. Chem. Res. 2014, 23, 127.
[19] Hosseinzadeh, R.; Tajbakhsh, M.; Mohadjerani, M.; Alikarami, M. J. Chem. Sci. 2010, 122, 143.
[20] Massah, A. R.; Sayadi, S.; Ebrahimi, S. RSC Adv. 2012, 2, 6606.
[21] Zhang, W.; Xie, J.; Rao, B.; Luo, M. J. Org. Chem. 2015, 80, 3504.
[22] Chen, K.; Chen, W.; Han, B.; Chen, W.; Liu, M.; Wu, H. Org. Lett. 2020, 22, 1841.
[23] Burmistrov, S. I. Ukr. Fiz. Zh. 1966, 32, 601.
[24] Krasavin, I. A. Metody Polycheniya Khim. Reaktivov i Preparatov, Gos. Kom. Sov. Min. SSSR po Khim. 1962, 4~5, 69.
[25] Ueda, Y.; Yano, H.; Momose, T. Chem. Pharm. Bull. 1964, 12, 5.
[26] Shekhar, S. X.; Dunn, T. B.; Kotecki, B. J.; Montavon, D. K.; Cullen, S. C. J. Org. Chem. 2011, 76, 4552.
[27] Gowda, B. T.; Jayalakshmi, K. L.; Shetty, M. Z. Naturforsch. 2004, 59a, 239.
[28] You, C. R.; Yao, F.; Yan, T.; Cai, M. C. RSC Adv. 2016, 6, 43605.
[29] Namba, K.; Zheng, X.; Motoshima, K.; Kobayashi, H.; Tai, A.; Takahashi, E.; Sasaki, K.; Okamoto, K.; Kakuta, H. Bioorg. Med. Chem. 2008, 16, 6131.
[30] Ueda, Y.; Yano, H.; Momose, T. Chem. Pharm. Bull. 1964, 12, 5.
[31] Cremlyn, R. J.; Goulding, K. H.; Swinbourne, F. J.; Yung, K. M. Phosphorus Sulfur 1981, 10, 111.
[32] Solov'ev, M. Y.; Filimonov, S. I.; Skorenko, A. V.; Ivanenkov, Ya. A.; Balakin, K. B.; Dorogov, M. V. Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 2004, 47, 28.
[33] Kostsova, A. G. Zh. Obshch. Khim. 1953, 23, 949.
[34] Maghsoodia, N. K.; Khazaelia, T.; Massah, A. R. J. Chem. Res. 2015, 39, 141.
[35] Pantaine, L.; Richard, F.; Marrot, J.; Moreau, X.; Coeffard, V.; Grecka, C. Adv. Synth. Catal. 2016, 358, 2012.
[36] Johnson, C. R.; Jonsson, E. U.; Bacon, C. C. J. Org. Chem. 1979, 44, 2055.
[37] Gregg, D. C.; Blood, C. A., Jr. J. Org. Chem. 1951, 16, 1255.
[38] Bonk, J. D.; Amos, D. T.; Olson, S. J. Synth. Commun. 2007, 37, 2039.
[39] Illuminati, G. J. Am. Chem. Soc. 1956, 78, 2603.
[40] Amorosa, I. M. Farmaco 1949, 4, 290.
[41] Yale, H.; Sowinski, F. J. Org. Chem. 1960, 25, 1824.
[42] Isozaki, M. Tokyo Kogyo Shikensho Hokoku 1950, 45, 295.
[43] Baker, Robert H.; Dodson, R. M.; Riegel, B. J. Am. Chem. Soc. 1946, 68, 2636.
[44] Chhabra, S. R.; Mahajan, A.; Chan, W. C. J. Org. Chem. 2002, 67, 4017.
[45] Tota, A.; John-Campbell, S. S.; Briggs, E. L.; Estevez, G. O.; Afonso, M.; Degennaro, L.; Luisi, R.; J. A. Org. Lett. 2018, 20, 2599.
[46] Maslankiewicz, A.; Marciniec, K.; Pawlowski, M.; Zajdel, P. Heterocycles 2007, 71, 1975.
[47] Moroda, A.; Togo, H. Tetrahedron 2006, 62, 12408.
[48] Field, L.; Grunwald, F. A. J. Am. Chem. Soc. 1953, 75, 934.
[49] Truce, W. E.; Gunberg, P. F. J. Am. Chem. Soc. 1950, 72, 2401.

高价碘试剂促进的N-芳基磺酰胺类化合物脱芳基反应

Hypervalent Organoiodine Promoted Dearylation Reaction of N-Aryl Sulfonamides

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