One-Pot Synthesis of Diaryl Sulfonamides using an Iron- and Copper-Catalyzed Aryl C–H Amidation Process

Lachlan J. N. Waddell; Martyn C. Henry; Mohamed A. B. Mostafa; Andrew Sutherland

doi:10.1055/a-1884-6988

Synthesis, Table of Contents

Synthesis 2022; 54(20): 4551-4560
DOI: 10.1055/a-1884-6988

paper

One-Pot Synthesis of Diaryl Sulfonamides using an Iron- and Copper-Catalyzed Aryl C–H Amidation Process

Authors

Lachlan J. N. Waddell

^aSchool of Chemistry, Joseph Black Building, University of Glasgow, Glasgow, G12 8QQ, UK
Martyn C. Henry

^aSchool of Chemistry, Joseph Black Building, University of Glasgow, Glasgow, G12 8QQ, UK
Mohamed A. B. Mostafa

^aSchool of Chemistry, Joseph Black Building, University of Glasgow, Glasgow, G12 8QQ, UK
Andrew Sutherland ∗

^aSchool of Chemistry, Joseph Black Building, University of Glasgow, Glasgow, G12 8QQ, UK

Abstract

All articles of this category

Abstract

A one-pot, two-stage synthesis of diaryl sulfonamides using sequential iron and copper catalysis is developed. Regioselective para-iodination of activated arenes by the super Lewis acid, iron triflimide and N-iodosuccinimide (NIS), is followed by a copper(I)-catalyzed N-arylation reaction. The process is found to be applicable for the coupling of a range of anisoles, anilines and acetanilides with primary sulfonamides and is used for the one-pot synthesis of biologically important compounds.

Key words

sulfonamides - iron catalysis - copper catalysis - aryl substitution

Full Text

References

References

1a Drews J. Science 2000; 287: 1960
1b Smith DA, Jones RM. Curr. Opin. Drug. Discovery Dev. 2008; 11: 72
1c Bentley R. J. Ind. Microbiol. Biotechnol. 2009; 36: 775

2a Vicente-Blázquez A, González M, Álvarez R, del Mazo S, Medarde M, Peláez R. Med. Res. Rev. 2019; 39: 775
2b Elgemeie GH, Azzam RA, Elsayed RE. Med. Chem. Res. 2019; 28: 1099
2c El-Gaby MS. A, Ammar YA, El-Qaliei MI. H, Ali AM, Hussein MF, Faraghally FA. Egypt J. Chem. 2020; 63: 5289

3 Sparks SM, Chen G, Collins JL, Danger D, Dock ST, Jayawickreme C, Jenkinson S, Laudeman C, Leesnitzer MA, Liang X, Maloney P, McCoy DC, Moncol D, Rash V, Rimele T, Vulimiri P, Way JM, Ross S. Bioorg. Med. Chem. Lett. 2014; 24: 3100

4a Li Q, Sham H, Woods KW, Steiner BA, Gwaltney SL. II, Barr KJ, Imade HM, Rosenberg S. US Patent 6521658, 2003
4b González M, Ovejero-Sánchez M, Vicente-Blázquez A, Medarde M, González-Sarmiento R, Peláez R. J. Enzyme Inhib. Med. Chem. 2021; 36: 1029

5 Medina JC, Shan B, Beckmann H, Farrell RP, Clark DL, Learned RM, Roche D, Li A, Baichwal V, Case C, Baeuerle PA, Rosen T, Jaen JC. Bioorg. Med. Chem. Lett. 1998; 8: 2653

6a Fish PV, Filippakopoulos P, Bish G, Brennan PE, Bunnage ME, Cook AS, Federov O, Gerstenberger BS, Jones H, Knapp S, Marsden B, Nocka K, Owen DR, Philpott M, Picaud S, Primiano MJ, Ralph MJ, Sciammetta N, Trzupek JD. J. Med. Chem. 2012; 55: 9831
6b Fish PV, Cook AS, Phillips C, Bent AF, Mills JE. J, Sciammetta N. WO2013027168 A1, 2013

7 For a review, see: Kolaczek A, Fusiarz I, Lawecka J, Branowska D. CHEMIK 2014; 68: 620

For example, see:

8a Kim J.-G, Jang DO. Synlett 2007; 2501
8b Bahrami K, Khodaei MM, Soheilizad M. J. Org. Chem. 2009; 74: 9287
8c Zhang W, Xie J, Rao B, Luo M. J. Org. Chem. 2015; 80: 3504
8d Flegeau EF, Harrison JM, Willis MC. Synlett 2016; 27: 101
8e Mukherjee P, Woroch CP, Cleary L, Rusznak M, Franzese RW, Reese MR, Tucker JW, Humphrey JM, Etuk SM, Kwan SC, Ende CW, Ball ND. Org. Lett. 2018; 20: 3943
8f Chen Y, Murray RD, Davies AT, Willis MC. J. Am. Chem. Soc. 2018; 140: 8781
8g Chen K, Chen W, Han B, Chen W, Liu M, Wu H. Org. Lett. 2020; 22: 1841

9 Rosen BR, Ruble JC, Beauchamp TJ, Navarro A. Org. Lett. 2011; 13: 2564
10 Shekhar S, Dunn TB, Kotecki BJ, Montavon DK, Cullen SC. J. Org. Chem. 2011; 76: 4552

11a Lam PY. S, Vincent G, Clark CG, Deudon S, Jadhav PK. Tetrahedron Lett. 2001; 42: 3415
11b Deng W, Liu L, Zhang C, Liu M, Guo Q.-X. Tetrahedron Lett. 2005; 46: 7295

12a Xiao B, Gong T.-J, Xu J, Liu Z.-J, Liu L. J. Am. Chem. Soc. 2011; 133: 1466
12b John A, Nicholas KM. J. Org. Chem. 2011; 76: 4158
12c Zhao H, Shang Y, Su W. Org. Lett. 2013; 15: 5106
12d Shang M, Sun S.-Z, Dai H.-X, Yu J.-Q. J. Am. Chem. Soc. 2014; 136: 3554
12e Maiden TM. M, Swanson S, Procopiou PA, Harrity JP. A. J. Org. Chem. 2016; 81: 10641
12f Song C, Wang T, Yu T, Cui D.-M, Zhang C. Org. Biomol. Chem. 2017; 15: 7212
12g Zhang W, Yang D, Wang W, Wang S, Zhao H. Eur. J. Org. Chem. 2018; 2071
12h Liu L, Wang N, Dai C, Han Y, Yang S, Huang Z, Zhao Y. Eur. J. Org. Chem. 2019; 7857

13 Racys DT, Warrilow CE, Pimlott SL, Sutherland A. Org. Lett. 2015; 17: 4782

14a Antoniotti S, Dalla V, Duñach E. Angew. Chem. Int. Ed. 2010; 49: 7860
14b Earle MJ, Hakala U, McAuley BJ, Nieuwenhuyzen M, Ramani A, Seddon KR. Chem. Commun. 2004; 1368

15 Mostafa MA. B, Bowley RM, Racys DT, Henry MC, Sutherland A. J. Org. Chem. 2017; 82: 7529

16a Mostafa MA. B, Calder ED. D, Racys DT, Sutherland A. Chem. Eur. J. 2017; 23: 1044
16b Henry MC, Senn HM, Sutherland A. J. Org. Chem. 2019; 84: 346
16c Henry MC, Sutherland A. Org. Lett. 2020; 22: 2766

For reviews of copper-catalyzed aryl amination, see:

17a Kunz K, Scholz U, Ganzer D. Synlett 2003; 2428
17b Ley SV, Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400
17c Sambiagio C, Marsden SP, Blacker AJ, McGowan PC. Chem. Soc. Rev. 2014; 43: 3525
17d Okano K, Tokuyama H, Fukuyama T. Chem. Commun. 2014; 50: 13650

18 Racys DT, Sharif SA. I, Pimlott SL, Sutherland A. J. Org. Chem. 2016; 81: 772
19 It should be noted that in a previous study (see reference 16b), we performed DFT calculations using Fukui functions, which provided a molecular orbital rationale for the high para regioselectivity observed for iron triflimide catalyzed halogenation of arenes.
20 Klapars A, Antilla JC, Huang X, Buchwald SL. J. Am. Chem. Soc. 2001; 123: 7727
21 As previously reported (see references 13, 15 and 16), electron-rich arenes are required for the iron(III)-catalyzed halogenation step. Electron-deficient arenes are not substrates for this transformation.
22 Xu F, Zhao Y, Zhou H, Li C, Zhang X, Hou T, Qu L, Wei L, Wang J, Liu Y, Liang X. Bioorg. Med. Chem. Lett. 2020; 30: 127650
23 Antilla JC, Klapars A, Buchwald SL. J. Am. Chem. Soc. 2002; 124: 11684
24 Nasrollahzadeh M, Ehsani A, Maham M. Synlett 2014; 25: 505
25 Yang K, Ke M, Lin Y, Song Q. Green Chem. 2015; 17: 1395
26 Kato T, Okamoto I, Tanatani A, Hatano T, Uchiyama M, Kagechika H, Masu H, Katagiri K, Tominaga M, Yamaguchi K, Azumaya I. Org. Lett. 2006; 8: 5017
27 Nasrollahzadeh M, Rostami-Vartooni A, Ehsani A, Moghadam M. J. Mol. Catal. A: Chem. 2014; 387: 123
28 Pan C, Cheng J, Wu H, Ding J, Liu M. Synth. Commun. 2009; 39: 2082
29 Lawrence HR, Kazi A, Luo Y, Kendig R, Ge Y, Jain S, Daniel K, Santiago D, Guida WC, Sebti SM. Bioorg. Med. Chem. 2010; 18: 5576
30 Arcoria A, Maccarone E, Musumarra G, Tomaselli GA. J. Org. Chem. 1973; 38: 2457
31 Rahaim RJ. Jr, Maleczka RE. Jr. Synthesis 2006; 3316
32 Deruer E, Coulibali S, Boukercha S, Canesi S. J. Org. Chem. 2017; 82: 11884
33 Yu C, Liu B, Hu L. J. Org. Chem. 2001; 66: 919
34 Ouyang B, Liu D, Xia K, Zheng Y, Mei H, Qiu G. Synlett 2018; 29: 111
35 Jiang ZY, Xu L, Lu MC, Chen ZY, Yuan ZW, Xu XL, Guo XK, Zhang XJ, Sun HP, You QD. J. Med. Chem. 2015; 58: 6410

Supplementary Material

Supporting Information (PDF) (opens in new window)