SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2024 , Vol. 44 >Issue 2: 533 - 549

DOI: https://doi.org/10.6023/cjoc202310005

ARTICLES

Isoamyl Nitrite Activated Primary Sulfonamide to Sulfonyl Bromide and Sulfonyl Chloride

  • Gangzhong Jiang ,
  • Jiaxing Lin ,
  • Xiaoguang Bao ,
  • Xiaobing Wan
Expand
  • College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123
* Corresponding authorss. E-mail: ;

Received date: 2023-10-07

  Revised date: 2023-11-02

  Online published: 2023-11-08

Supported by

Natural Science Foundation of China(21973068); Natural Science Foundation of China(21971175)

Fold

Abstract

Sulfonyl bromide and sulfonyl chloride are important compounds commonly used as building blocks in organic synthesis. This paper presents the successful synthesis of sulfonyl bromide or sulfonyl chloride from primary sulfonamide using isoamyl nitrite (iAmONO) as an activator, dibromantine (DBDMH) as a bromine source, or trichloroisocyanuric acid (TCCA) as a chlorine source. The method offers several advantages such as wide range of raw materials, compatibility with various substrates, high yield, and mild reaction conditions. It is suitable for both gram-scale preparations and subsequent derivations, demonstrating practical value. Mechanistic studies suggest that N,N-dihalosulfonamide is a potential intermediate in this process and isoamyl nitrite plays a crucial role in the conversion process.

Key words： primary sulfonamide; isoamyl nitrite; sulfonyl bromide; sulfonyl chloride

Cite this article

Gangzhong Jiang , Jiaxing Lin , Xiaoguang Bao , Xiaobing Wan . Isoamyl Nitrite Activated Primary Sulfonamide to Sulfonyl Bromide and Sulfonyl Chloride[J]. Chinese Journal of Organic Chemistry, 2024 , 44(2) : 533 -549 . DOI: 10.6023/cjoc202310005

References

[1]
Liu, L. Y.; Sun, T.; Liu, Y.; Sun, Y. Y.; Ma, F. Z. Nephro. 2019, 141, 1.
[2]
McCune, J. S.; Navarro, S. L.; Baker, K. S.; Risler, L. J.; Phillips, B. R.; Randolph, T. W.; Shireman, L.; Schoch, H. G.; Deeg, H. J.; Zhang, Y.; Men, A.; Maton, L.; Huitema, A. D. R. Clin. Pharmacol. The. 2023, 113, 370.
[3]
Long, G. V.; Flaherty, K. T.; Stroyakovskiy, D.; Gogas, H.; Levchenko, E.; de Braud, F.; Larkin, J.; Garbe, C.; Jouary, T.; Hauschild, A.; Chiarion-Sileni, V.; Lebbe, C.; Mandala, M.; Millward, M.; Arance, A.; Bondarenko, I.; Haanen, J.; Hansson, J.; Utikal, J.; Ferraresi, V.; Mohr, P.; Probachai, V.; Schadendorf, D.; Nathan, P.; Robert, C.; Ribas, A.; Davies, M. A.; Lane, S. R.; Legos, J. J.; Mookerjee, B.; Grob, J. J. Ann. Oncol. 2017, 28, 1631.
[4]
(a) Fan, Y.; He, Y.; Liu, X.; Hu, T.; Ma, H.; Yang, X.; Luo, X.; Huang G. Chen, R.; Xu, S.; Shen, F.; Xu, C.; Wang, K.; Wang, Z.; Liu, L. Molecule. 2021, 26, 5551.
[4]
(b) Poshkus, A. C.; Herweh, J. E.; Magnotta, F. A. J. Org. Chem. 1963, 28, 2766.
[4]
(c) Terentév, A. O.; Mulina, O. M.; Parshin, V. D.; Kokorekin, V. A.; Nikishin, G. I. Org. Biomol. Chem. 2019, 17, 3482.
[5]
(a) Platonov, V. E.; Bredikhin, R. A.; Maksimov, A. M.; Kireenkov, V. V. J. Fluorine Chem. 2010, 131, 13.
[5]
(b) Madabhushi, S.; Jillella, R.; Sriramoju, V.; Singh, R. Green Chem. 2014, 16, 3125.
[5]
(c) Jereb, M.; Hribernik, L. Green Chem. 2017, 19, 2286.
[5]
(d) Silva-Cuevas, C.; Perez-Arrieta, C.; Polindara-García, L. A.; Lujan-Montelongo, J. A. Tetrahedron Lett. 2017, 58, 2244.
[5]
(e) Kirihara, M.; Yamahara, S.; Okada, T.; Matsumuro, H.; Kinoshita, Y.; Kitajima, A.; Takamura, Y.; Odagiri, T.; Asawa, T.; Sugiyama, Y.; Kimura, Y. Synthesi. 2022, 54, 4120.
[6]
(a) Fu, L. L.; Bao, X. D.; Li, S. S.; Wang, L. T.; Liu, Z. G.; Chen, W. Z.; Xia, Q. Q.; Liang, G. Tetrahedro. 2017, 73, 2504.
[6]
(b) Sarkar, D.; Ghosh, M. K.; Rout, N. Tetrahedron Lett. 2018, 59, 2360.
[7]
Majek, M.; Neumeier, M.; Jacobi von Wangelin, A. ChemSusChe. 2017, 10, 151.
[8]
Gomez-Palomino, A.; Cornella, J. Angew. Chem.. Int. Ed. 2019, 58, 18235.
[9]
Markushyna, Y.; Schü?lbauer, C. M.; Ullrich, T.; Guldi, D. M.; Antonietti, M.; Savateev, A. Angew. Chem.. Int. Ed. 2021, 60, 20543.
[10]
Timmer, B. J. J.; Schaufelberger, F.; Hammarberg, D.; Franzen, J.; Ramstrom, O.; Diner, P. J. Chem. Educ. 2018, 95, 1301.
[11]
Fier, P. S.; Kim, S.; Maloney, K. M. J. Am. Chem. Soc. 2019, 141, 18416.
[12]
(a) Jia, X.; Li, P. Synthesi. 2017, 50, 711.
[12]
(b) Yang, X. B.; Shi, L. L.; Fu, H. Synlet. 2014, 25, 847.
[12]
(c) Shen, B. R.; Annamalai, P.; Bai, R.; Badsara, S. S.; Lee, C. F. Org. Lett. 2022, 24, 5988.
[12]
(d) Sirvinskaite, G.; Reisenbauer, J. C.; Morandi, B. Chem. Sci. 2023, 14, 1709.
[12]
(e) Sau, P.; Rakshit, A.; Alam, T.; Srivastava, H. K.; Patel, B. K. Org. Lett. 2019, 21, 4966.
Options
Outlines

/

〈 〉