Chromatography-Free and Eco-Friendly Synthesis of Aryl Tosylates and Mesylates

Abstract

Two chromatography-free and eco-friendly protocols have been developed to synthesize aryl tosylates and mesylates by the tosylation and mesylation of the corresponding hydroxyarenes, respectively. These protocols are superior to other known ones regarding the simplicity, reaction time and conditions, the range of substrates, yields, and environmental friendliness.

Key words

aryl tosylates - aryl mesylates - tosylation - mesylation - green chemistry

• References

• 1a Fujikawa N, Ohta T, Yamaguchi T, Fukuda T, Ishibashi F, Iwao M. Tetrahedron 2006; 62: 594
• 1b Quiroz-Florentino H, Hernández-Benitez RI, Aviña JA, Burgueño-Tapia E, Tamariz J. Synthesis 2011; 1106
• 1c Grandane A, Belyakov S, Zalubovskis PT. R. Tetrahedron 2012; 68: 5541
• 1d Mao PC.-M, Mouscadet J.-F, Leh H, Auclair C, Hsu L.-Y. Chem. Pharm. Bull. 2002; 50: 1634
• 1e Hugo AG, Jimena MM, Gladys MC, Carlos ET, Carlos RP. Bioorg. Med. Chem. Lett. 2014; 24: 760
• 1f Xu H, Zhang J.-L. Bioorg. Med. Chem. Lett. 2011; 21: 5177
• 1g Ueno T, Schlegel L, Hayashi N, Shiraishi H, Iwayanagi T. Polym. Eng. Sci. 1992; 32: 1511
• 2a Hu F, Lei X. Tetrahedron 2014; 70: 3854
• 2b Park NH, Teverovskiy G, Buchwald SL. Org. Lett. 2014; 16: 220
• 2c Nishihara Y, Ogawa D, Noyori S, Iwasaki M. Chem. Lett. 2012; 41: 1503
• 2d Percec V, Golding GM, Smidrkal J, Weichold O. J. Org. Chem. 2004; 69: 3447
• 2e Tang Z.-Y, Hu Q.-S. J. Am. Chem. Soc. 2004; 126: 3058
• 2f Zim D, Lando VR, Dupont J, Monteiro AL. Org. Lett. 2001; 3: 3049
• 2g Percec V, Bae J.-Y, Zhao M, Hill DH. J. Org. Chem. 1995; 60: 176
• 3a Meshram GA, Patil VD. Tetrahedron Lett. 2009; 50: 1117
• 3b Kim J.-G, Jang DO. Synlett 2007; 2501
• 4 Xu L.-W, Xia C.-G. Synth. Commun. 2004; 34: 1199
• 5 Zhao N, Li Y, Wang Y, Wang J. J. Sulfur Chem. 2006; 27: 427
• 6 Fazaeli R, Tangestaninejad S, Aliyan H. Can. J. Chem. 2006; 84: 812
• 7 Bahrami K, Khodaei MM, Abbasi J. Tetrahedron 2012; 68: 5095
• 8 Liu H, Xie Y, Gu Y. Tetrahedron Lett. 2011; 52: 4324
• 9 Kaboudin B, Abedi Y. Synthesis 2009; 2025
• 10 Barbero M, Degani I, Dughera S, Fochi R, Perracino P. Synthesis 1998; 90
• 11a Zim D, Lando VR, Dupont J, Monteiro AL. Org. Lett. 2001; 3: 3049
• 11b Gooßen LJ, Rodríguez N, Lange PP, Linder C. Angew. Chem. Int. Ed. 2010; 49: 1111
• 11c Munday RH, Martinelli JR, Buchwald SL. J. Am. Chem. Soc. 2008; 130: 2754
• 11d Schade MA, Metzger A, Hug S, Knochel P. Chem. Commun. 2008; 3046
• 11e R’kyek O, Halland N, Lindenschmidt A, Alonso J, Lindemann P, Urmann M, Nazare M. Chem. Eur. J. 2010; 16: 9986
• 11f Korn TJ, Schade MA, Cheemala MN, Wirth S, Guevara SA, Cahiez G, Knochel P. Synthesis 2006; 3547
• 11g Kuroda J.-I, Inamoto K, Hiroya K, Doi T. Eur. J. Org. Chem. 2009; 2251
• 12a Grandāne A, Mishnev AF, Vozny IV, Žalubovskis R. Chem. Heterocycl. Compd. 2012; 48: 974
• 12b So CM, Lau CP, Kwong FY. Angew. Chem. Int. Ed. 2008; 47: 8059
• 12c Mori A, Mizusaki T, Ikawa T, Maegawa T, Monguchi Y, Sajiki H. Tetrahedron 2007; 63: 1270
• 12d Wilson DA, Wilson CJ, Moldoveanu C, Resmerita A.-M, Corcoran P, Hoang LM, Rosen BM, Percec V. J. Am. Chem. Soc. 2010; 132: 1800
• 12e Leowanawat P, Zhang N, Percec V. J. Org. Chem. 2012; 77: 1018
• 12f Chang JW. W, Chia EY, Chai CL. L, Seayad J. Org. Biomol. Chem. 2012; 10: 2289
• 12g Ritter T, Stanek K, Larrosa I, Carreira EM. Org. Lett. 2004; 6: 1513
• 12h Wazeer MI. M, Ali SA, Arab M. Spectrochim. Acta A 1987; 43: 843
• 13 Asano K, Matsubara S. Org. Lett. 2009; 11: 1757
• 14a Alfonsi K, Colberg J, Dunn PJ, Fevig T, Jennings S, Johnson TA, Kleine HP, Knight C, Perry MA. N. D. A, Stefaniak M. Green Chem. 2008; 10: 31
• 14b Henderson RK, Jiménez-González C, Constable DJ. C, Alston SR, Inglis GG. A, Fisher G, Sherwood J, Binks SP, Curzons AD. Green Chem. 2011; 13: 854
• 14c Prat D, Pardigon O, Flemming H.-W, Letestu S, Ducandas V, Isnard P, Guntrum E, Senac T, Ruisseau S, Cruciani P, Hosek P. Org. Process Res. Dev. 2013; 17: 1517
• 15 Mertens MD, Pietsch M, Schnakenburg G, Gütschow M. J. Org. Chem. 2013; 78: 8966
• 16 Yoshida Y, Sakakura Y, Aso N, Okada S, Tanabe Y. Tetrahedron 1999; 55: 2183
• 17a Casiraghi G, Casnati G, Pochini A, Puglia G, Ungaro R, Sartori G. Synthesis 1981; 143
• 17b Sartori G, Bigi F, Maggi R, Porta C. Tetrahedron Lett. 1994; 35: 7073
• 18 So CM, Lee HW, Lau CP, Kwong FY. Org. Lett. 2009; 11: 317