SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 8: 2433 - 2441

DOI: https://doi.org/10.6023/cjoc202001007

Hypervalent Organoiodine Promoted Dearylation Reaction of N-Aryl Sulfonamides

  • Song Mengmeng ,
  • Zhang Zhiguo ,
  • Zheng Dan ,
  • Li Xiang ,
  • Liang Rui ,
  • Zhao Xu'na ,
  • Shi Lei ,
  • Zhang Guisheng
Expand
  • 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 date: 2020-01-04

  Revised date: 2020-05-16

  Online 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).

Fold

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 . DOI: 10.6023/cjoc202001007

References

[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.
Options
Outlines

/

〈 〉