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DOI: 10.1055/a-2360-9229
Thiourea/NCBSI/HCl System: Telescoping Alkyl Halide to Alkyl Sulfonyl Chloride by Recyclable N-Chloro-N-(phenylsulfonyl)benzene Sulfonamide (NCBSI)
Financial support was provided by Chhatrapati Shahu Maharaj Research, Training, and Human Development Institute, Govt. of Maharashtra, India (CSMNRF-2022/2022-23/2341).
Abstract
A convenient and efficient method to synthesize diverse alkyl sulfonyl chlorides through N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)-mediated oxidative chlorosulfonation of S-alkyl isothiouronium salts obtained from alkyl chlorides is presented. Synthesizing structurally diverse alkyl sulfonyl chloride in moderate to excellent yields up to 98% from alkyl halide was achieved via easy formation of S-alkyl isothiouronium salts using inexpensive thiourea. The mild reaction conditions and broad substrate scope make this method attractive for alkylsulfonyl chloride syntheses.
Key words
alkyl sulfonyl chlorides - N-chloro-N-(phenylsulfonyl)benzene sulfonamide - S-alkyl isothiouronium salts - alkyl halides - chlorosulfonationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2360-9229.
- Supporting Information
Publikationsverlauf
Eingereicht: 27. September 2023
Angenommen nach Revision: 05. Juli 2024
Accepted Manuscript online:
16. Juli 2024
Artikel online veröffentlicht:
26. August 2024
© 2024. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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References
- 1 Zajac M, Peters R. Org. Lett. 2007; 9: 2007
- 2 Koch FM, Peters R. Angew. Chem. Int. Ed. 2007; 46: 2685
- 3a Sasmal PK, Ramachandran G, Zhang Y, Liu Z. Results Chem. 2021; 3: 100173
- 3b Kumar BS, Bhirud S, Chandrasekhar B, Kale S. US Patent 0084814 A1, 2006
- 4 Lee KL, Foley MA, Chen L, Behnke ML, Lovering FE, Kirincich SJ, McKew JC. J. Med. Chem. 2007; 50: 1380
- 5a Condon JS, Joseph-McCarthy D, Levin JI, Lombart HG, Lovering FE, Sun L, Zhang Y. Bioorg. Med. Chem. Lett. 2007; 17: 34
- 5b Eze FU, Ezeorah CJ, Ogboo BC, Okpareke OC, Rhyman L, Ramasami P, Ugwu DI. Molecules 2022; 27: 7400
- 5c Davies TQ, Tilby MJ, Skolc D, Hall A, Willis MC. Org. Lett. 2020; 22: 9495
- 5d Chen R, Xu S, Shen F, Xu C, Wang K, Wang Z, Liu L. Molecules 2021; 26: 5551
- 6 Sohmiya H, Kimura T, Fujita M, Ando T. Chem. Lett. 1992; 21: 891
- 7 Blotny G. Tetrahedron Lett. 2003; 44: 1499
- 8 Yang Z, Zheng Y, Xu J. Synlett 2013; 24: 2165
- 9 Yang Z, Zhou B, Xu J. Synthesis 2014; 46: 225
- 10 Qiu K, Wang R. Synthesis 2015; 47: 3186
- 11a Markushyna Y, Schüßlbauer CM, Ullrich T, Guldi DM, Antonietti M, Savateev A. Angew. Chem. Int. Ed. 2021; 60: 20543
- 11b Silva-Cuevas C, Perez-Arrieta C, Polindara-García LA, Lujan-Montelongo JA. Tetrahedron Lett. 2017; 58: 2244
- 11c Sohrabnezhad S, Bahrami K, Hakimpoor F. J. Sulfur Chem. 2019; 40: 256
- 11d Nishiguchi A, Maeda K, Miki S. Synthesis 2006; 4131
- 11e Kutchin AV, Rubtsova SA, Lezina OM, Sudarikov DV, Frolova LL, Loginova IV, Grebyonkina ON. Pure Appl. Chem. 2017; 89: 1379
- 11f Bahrami K, Khodaei MM, Soheilizad M. J. Org. Chem. 2009; 74: 9287
- 12a Gómez-Palomino A, Cornella J. Angew. Chem. Int. Ed. 2019; 131: 18403
- 12b Hardstaff WR, Langler RF, Leahy J, Newman MJ. Can. J. Chem. 1975; 53: 2664
- 12c Shcherbakova I, Pozharskii AF. Alkyl Chalcogenides: Sulfur-Based Functional Groups. In Comprehensive Organic Functional Group Transformations II. Pergamon; Oxford: 2004: 89-235
- 12d Johnson TB, Sprague JM. J. Am. Chem. Soc. 1936; 58: 1348
- 13a Fujita S. Synthesis 1982; 423
- 13b Castang S, Chantegrel B, Deshayes C, Dolmazon R, Gouet P, Haser R, Reverchon S, Nasser W, Doutheau A. Bioorg. Med. Chem. Lett. 2004; 14: 5145
- 13c Bahrami K, Khodaei M, Abbasi J. Tetrahedron 2012; 5095
- 14 Gilbert EE. Synthesis 1969; 3
- 15a Misal B, Palav A, Ganwir P, Chaturbhuj G. Tetrahedron Lett. 2021; 63: 152689
- 15b Palav A, Misal B, Ganwir P, Badani P, Chaturbhuj G. Tetrahedron Lett. 2021; 73: 153094
- 16a Wenzel TJ, Zaia J. Anal. Chem. 1987; 59: 562
- 16b Hemalatha P, Kumaresan S, Veeravazhuthi V, Gunasekaran S. Spectrochim. Acta, Part A 2013; 109: 1
- 16c Hemalatha P, Veeravazhuthi V, Mallika J, Narayandass SK, Mangalaraj D. Cryst. Res. Technol. 2006; 1: 775
- 17 Yang Z, Xu J. Org. Synth. 2014; 91: 11
- 18 Lee I, Kang HK, Lee HW. J. Am. Chem. Soc. 1987; 109: 7472
- 19 Kim DW, Ko YK, Kim SH. Synthesis 1992; 1203
- 20 Nan X, Jiang YF, Li HJ, Wang JH, Wu YC. Bioorg. Med. Chem. 2019; 27: 2801
- 21 Górski B, Basiak D, Talko A, Basak T, Mazurek T, Barbasiewicz M. Eur. J. Org. Chem. 2018; 1774
- 22 Alapafuja SO, Nikas SP, Bharathan IT, Shukla VG, Nasr ML, Bowman AL, Makriyannis A. J. Med. Chem. 2012; 55: 10074
- 23 Nguyen VT, Haug GC, Nguyen VD, Vuong NT, Karki GB, Arman HD, Larionov OV. Chem. Sci. 2022; 13: 4170