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Synthesis 2024; 56(21): 3253-3260
DOI: 10.1055/a-2295-8639
DOI: 10.1055/a-2295-8639
paper
Special Issue PSRC-10 (10th Pacific Symposium on Radical Chemistry)
Denitrative Sulfonylation of Nitroarenes with Sodium Sulfinates
J.D.L. and B.D.C. thank The University of Manchester for PhD studentships. M.Č. thanks the National Scholarship Programme of the Slovak Republic (Slovak Academic Information Agency) and the Slovak University of Technology in Bratislava for financial support. T.D.H. thanks AstraZeneca for a PhD studentship. E.R.X.L. thanks the EPSRC Centre for Doctoral Training in Integrated Catalysis (EPSRC grant: EP/S023755/1) for a PhD studentship.
Abstract
A one-step method to convert nitroarenes into aryl sulfones under operationally simple, transition-metal-free conditions is described. A range of nitroarenes were reacted with sodium sulfinates and caesium carbonate in N,N′-dimethylpropyleneurea to afford aryl sulfones in up to 83% yield.
Key words
denitrative functionalisation - sulfonylation - nitroarenes - aryl sulfones - transition-metal-freeSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2295-8639.
- Supporting Information
Publication History
Received: 16 February 2024
Accepted after revision: 27 March 2024
Accepted Manuscript online:
27 March 2024
Article published online:
15 April 2024
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References
- 1a Dizman C, Tasdelen MA, Yagci Y. Polym. Int. 2013; 62: 991
- 1b Zhao C, Rakesh KP, Ravidar L, Fang W.-Y, Qin H.-L. Eur. J. Med. Chem. 2019; 162: 679
- 1c Jeanguenat A, Lamberth C. Pest Manage. Sci. 2023; 79: 2647
- 2a Liu N.-W, Liang S, Manolikakes G. Synthesis 2016; 48: 1939
- 2b Liang S, Hofman K, Friedrich M, Keller J, Manolikakes G. ChemSusChem 2021; 14: 4878
- 3a Olah GA, Kobayashi S, Nishimura J. J. Am. Chem. Soc. 1973; 95: 564
- 3b Singh RP, Kamble RM, Chandra KL, Saravanan P, Singh VK. Tetrahedron 2001; 57: 241
- 3c Nara SJ, Harjani JR, Salunkhe MM. J. Org. Chem. 2001; 66: 8616
- 3d Bahrami K, Khodei MM, Shahbazi F. Tetrahedron Lett. 2008; 49: 3931
- 3e Falconnet A, Arndt J, Hashmi AS. K, Schaub T. Eur. J. Org. Chem. 2022; e202200477
- 4a Yu B, Liu A.-H, He L.-N, Li B, Diao Z.-F, Li Y.-N. Green Chem. 2012; 14: 957
- 4b Jereb M. Green Chem. 2012; 14: 3047
- 4c Kim DH, Lee J, Lee A. Org. Lett. 2018; 20: 764
- 4d Liu K.-J, Deng J.-H, Yang J, Gong S.-F, Lin Y.-W, He J.-Y, Cao Z, He W.-M. Green Chem. 2020; 22: 433
- 5a Maloney KM, Kuethe JT, Linn K. Org. Lett. 2011; 13: 102
- 5b Umierski N, Manolikakes G. Org. Lett. 2013; 15: 188
- 5c Chen L, Liang J, Chen Z, Chen J, Yan M, Zhang X. Adv. Synth. Catal. 2019; 361: 956
- 5d Li Y, Liu T, Qiu G, Wu J. Adv. Synth. Catal. 2019; 361: 1154
- 5e Liang X, Li Y, Xia Q, Cheng L, Guo J, Zhang P, Zhang W, Wang Q. Green Chem. 2021; 23: 8865
- 6a Suzuki H, Abe H. Tetrahedron Lett. 1995; 36: 6239
- 6b Baskin JM, Wang Z. Org. Lett. 2002; 4: 4423
- 6c Zhu W, Ma D. J. Org. Chem. 2005; 70: 2696
- 6d Emmett EJ, Hayter BR, Willis MC. Angew. Chem. Int. Ed. 2013; 52: 12679
- 6e Yang M, Shen H, Li Y, Shen C, Zhang P. RSC Adv. 2014; 4: 26295
- 6f Yue H, Zhu C, Rueping M. Angew. Chem. Int. Ed. 2018; 57: 1371
- 6g Liu N.-W, Liang S, Margraf N, Shaaban S, Luciano V, Drost M, Manolikakes G. Eur. J. Org. Chem. 2018; 1208
- 6h Chen S, Li Y, Wang M, Jiang X. Green Chem. 2020; 22: 322
- 6i Yan Q, Cui W, Song X, Xu G, Jiang M, Sun K, Lv J, Yang D. Org. Lett. 2021; 23: 3663
- 6j Andrews JA, Willis MC. Synthesis 2022; 54: 1695
- 6k Mdluli V, Lehnherr D, Lam Y.-h, Ji Y, Newman JA, Kim J. Adv. Synth. Catal. 2023; 365: 3876
- 7 Ono N. The Nitro Group in Organic Synthesis . Wiley-VCH; Weinheim: 2001.
- 8a Hodgson HH. Chem. Rev. 1947; 40: 251
- 8b Galli C. Chem. Rev. 1988; 88: 765
- 8c Mo F, Dong G, Zhang Y, Wang J. Org. Biomol. Chem. 2013; 11: 1582
- 8d Mo F, Qiu D, Zhang Y, Wang J. Acc. Chem. Res. 2018; 51: 496
- 9a Muto K, Okita T, Yamaguchi J. ACS Catal. 2020; 10: 9856
- 9b Kashihara M, Nakao Y. Acc. Chem. Res. 2021; 54: 2928
- 10a Yadav MR, Nagaoka M, Kashihara M, Zhong RL, Miyazaki T, Sakaki S, Nakao Y. J. Am. Chem. Soc. 2017; 139: 9423
- 10b Inoue F, Kashihara M, Yadav MR, Nakao Y. Angew. Chem. Int. Ed. 2017; 56: 13307
- 10c Kashihara M, Yadav MR, Nakao Y. Org. Lett. 2018; 20: 1655
- 10d Asahara KK, Okita T, Saito AN, Muto K, Nakao Y, Yamaguchi J. Org. Lett. 2019; 21: 4721
- 10e Matsushita N, Kashihara M, Formica M, Nakao Y. Organometallics 2021; 40: 2209
- 10f Kashihara M, Kosaka K, Matsushita N, Notsu S, Osawa A, Nakao Y. Synlett 2023; 34: 1482
- 11a Kornblum N, Cheng L, Kerber RC, Kestner MM, Newton BN, Pinnick HW, Smith RG, Wade PA. J. Org. Chem. 1976; 41: 1560
- 11b Liang S, Zhang R.-Y, Xi L.-Y, Chen S.-Y, Yu X.-Q. J. Org. Chem. 2013; 78: 11874
- 11c Tian H, Cao A, Qiao L, Yu A, Chang J, Wu Y. Tetrahedron 2014; 70: 9107
- 12 Duff L, Meakin H, Richardson A, Greener AJ, Smith GW. A, Ocaña I, Chechik V, James MJ. Chem. Eur. J. 2023; 29: e202203807
- 13a Liang S, Hofman K, Friedrich M, Manolikakes G. Eur. J. Org. Chem. 2020; 4664
- 13b Reddy RJ, Kumari AH. RSC Adv. 2021; 11: 9130
- 14 Bulman Page PC, Wilkes RD, Reynolds D. In Comprehensive Organic Functional Group Transformations, Vol. 2, Chap. 3. Katritzky AR, Meth-Cohn O, Rees CW. Elsevier Science; Amsterdam: 1995: 113-275
- 15 Bock H, Lechner-Knoblauch U. Z. Naturforsch., B 1985; 40: 1463
- 16 Mondal S, Panda G. RSC Adv. 2014; 4: 28317
- 17 Yu B, Guo C.-X, Zhong C.-L, Diao Z.-F, He L.-N. Tetrahedron Lett. 2014; 55: 1818
- 18 Kinney RG, Arndtsen BA. Angew. Chem. Int. Ed. 2019; 58: 5085
- 19 Hethcox JC, Johnson HC, Kim J, Wang X, Cheng L, Cao Y, Tan M, DiRocco DA, Ji Y. Angew. Chem. Int. Ed. 2023; 62: e202217623
- 20 Liu T, Yu S, Shen X, Li Y, Liu J, Huang C, Cheng F. Synthesis 2022; 54: 153
- 21 Nandi GC. Synth. Commun. 2017; 47: 319
- 22 Gueye R, Pouget C, Champavier Y, Buxeraud J, Duroux J.-L, Fagnère C. C. R. Chim. 2014; 17: 443
For reviews, see:
For general reviews on the synthesis of aryl sulfones, see:
For examples of nucleophilic substitution reactions with sulfinate salts, see:
For examples of metal-catalysed coupling reactions with sulfinate salts, see:
For reviews on denitrative functionalisation, see:
For selected examples of denitrative functionalisation reactions, see: