Peracetic Acid Mediated sp² C–H Selenation of Arenes

^◊ Both authors contributed equally to this work.

Abstract

Peracetic acid promoted C–Se coupling reaction of arenes with diselenides under metal-free and solvent-free conditions has been described. The resulting selenide ethers were obtained in good to excellent yields. Peracetic acid provided the selenide ethers via sp² C–H selenation whereas previously in case of DTBP sp³ C–H selenation was observed.

Key words

peracetic acid - arenes - diselenides - C–Se coupling - selenide ethers

• References and Notes

• 1a Shamberger RJ In Biochemistry of Selenium . Plenum Press; New York: 1983
• 1b Klayman DL, Gunter HH In Organoselenium Compounds: Their Chemistry and Biology: Wiley-Interscience: New York, 1973 .
• 1c Rotruck JT, Pope AL, Ganther HE, Swanson AB, Hafeman DG, Hoekstra WG. Science 1973; 179: 588
• 1d Flohe L, Gunzler EA, Schock HH. FEBS Lett. 1973; 32: 132
• 1e Flohe L, Andreesen JR, Brigelius-Flohe R, Maiorino M, Ursini F. IUBMB Life 2000; 49: 411
• 1f Jacob C, Giles GI, Giles NM, Sies H. Angew. Chem. Int. Ed. 2003; 42: 4742
• 1g Sarma BK, Mugesh G. Org. Biomol. Chem. 2008; 6: 965
• 1h Nogueira CW, Zeni G, Rocha JB. T. Chem. Rev. 2004; 104: 6255
• 1i Mugesh G, du Mont WW, Sies H. Chem. Rev. 2001; 101: 2125
• 1j Mugesh G, Singh H. Chem. Soc. Rev. 2000; 29: 347
• 1k Patani GA, LaVoie EJ. Chem. Rev. 1996; 96: 3147
• 1l Abdo M, Zhang Y, Schramm VL, Knapp S. Org. Lett. 2010; 12: 2982
• 2a Braga AL, Barcellos T, Paixao MW, Deobald AM, Godoi M, Stefani HA, Cella R, Sharma A. Organometallics 2008; 27: 4009
• 2b Perin G, Lenardao EJ, Jacob RG, Panatieri RB. Chem. Rev. 2009; 109: 1277
• 3a Fukuzawa S.-i, Tsudsuki K. Tetrahedron: Asymmetry 1995; 6: 1039
• 3b Wirth T. Tetrahedron Lett. 1995; 36: 7849
• 3c Braga AL, Vargas F, Sehnem JA, Braga RC. J. Org. Chem. 2005; 70: 9021
• 3d Zielinska-Blajet M, Siedlecka R, Skarzewski J. Tetrahedron: Asymmetry 2007; 18: 131
• 3e Schwab RS, Soares LC, Dornelles L, Rodrigues OE. D, Paixao MW, Godoi M, Braga AL. Eur. J. Org. Chem. 2010; 3574
• 3f Vargas F, Sehnem JA, Galetto FZ, Braga AL. Tetrahedron 2008; 64: 392
• 3g Wirth T, Kulicke KJ, Fragale G. Helv. Chim. Acta 1996; 79: 1957
• 3h Wojaczynska E, Skazewski J. Tetrahedron: Asymmetry 2008; 19: 593

For reviews, see:
• 4a Wirth T. Tetrahedron 1999; 55: 1
• 4b Wirth T. Angew. Chem. Int. Ed. 2000; 39: 3740
• 4c Braga AL, Ludtke DS, Vargas F, Braga RC. Synlett 2006; 1453
• 4d Braga AL, Ludtke DS, Vargas F, Braga RC. Curr. Org. Chem. 2006; 10: 1921
• 4e Godoi M, Paixao MW, Braga AL. Dalton Trans. 2011; 40: 11347
• 5a Freudendahl DM, Iwaoka M, Wirth T. Eur. J. Org. Chem. 2010; 3934
• 5b Zhao L, Li Z, Wirth T. Eur. J. Org. Chem. 2011; 176
• 5c Shahzad SA, Vivant C, Wirth T. Org. Lett. 2010; 12: 1364
• 5d Braga AL, Zeni G, Andrade LH, Silveira CC. Synlett 1997; 595
• 5e Browne DM, Niyomura O, Wirth T. Org. Lett. 2007; 9: 3169
• 5f Tiecco M, Testaferri L, Tingoli M, Bagnoli L, Santi C. Synlett 1993; 798
• 6a Wirth T. Topics in Current Chemistry in Organoselenium Chemistry. Springer; Heidelberg: 2000: 208
• 6b Krief A In Comprehensive Organometallic Chemistry II . Vol. 11. Abel EV, Stone FG. A, Wilkinson G. Chap. 13 Pergamon Press; New York: 1995: 515
• 6c Paulmier C In Selenium Reagents and Intermediates in Organic Synthesis, Organic Chemistry Series 4. Baldwin JE. Pergamon Press; Oxford: 1986
• 7a Keck GE, Grier MC. Synlett 1999; 1657
• 7b Chen C, Crich D, Papadatos A. J. Am. Chem. Soc. 1992; 114: 8313
• 7c Boger DL, Mathvink RJ. J. Org. Chem. 1992; 57: 1429
• 7d Hiiro T, Morita Y, Inoue T, Kambe N, Ogawa A, Ryuand I, Sonoda N. J. Am. Chem. Soc. 1990; 112: 455
• 7e Sviridov AF, Erolenko MS, Yashunky DV, Kochetkov NK. Tetrahedron Lett. 1983; 24: 4355
• 8a Heppke G, Martens J, Praefcke K, Simon H. Angew. Chem., Int. Ed. Engl. 1977; 16: 318
• 8b Yamada J.-i, Akutsu H, Nishikawa H, Kikuchi K. Chem. Rev. 2004; 104: 5057
• 9a Inoue M, Yamahita S, Ishihara Y, Hirama M. Org. Lett. 2006; 8: 5805
• 9b Martin SF, Chen KX, Eary CT. Org. Lett. 1999; 1: 79
• 10a Stadman TC. Annu. Rev. Biochem. 1996; 65: 83
• 10b Muttenthaler M, Alewood PF. J. Pept. Chem. 2008; 14: 1223
• 11a Testaferri L, Tiecco M, Tingoli M, Chianelli D, Montanucci M. Synthesis 1983; 751
• 11b Suzuki H, Abe H, Suka V. Chem. Lett. 1981; 151
• 11c Pierini AB, Rossi RA. J. Org. Chem. 1979; 44: 4667
• 11d Rossi RA, Penenory AB. J. Org. Chem. 1981; 46: 4580
• 11e Grieco PA, Gilman S, Nishizawa M. J. Org. Chem. 1976; 41: 1458
• 12a Itoh T, Mase T. Org. Lett. 2004; 6: 4587
• 12b Murata M, Buchwald SL. Tetrahedron 2004; 60: 7397
• 12c Mispelaere-Canivet C, Spindler JF, Perrio S, Beslin P. Tetrahedron 2005; 61: 5253
• 12d Fernandez-Rodriguez MA, Shen QL, Hartwig JF. J. Am. Chem. Soc. 2006; 128: 2180
• 13a Cristau HJ, Chabaud B, Labaudiniere R, Christol H. Organometallics 1985; 4: 657
• 13b Percec V, Bae JY, Hill DH. J. Org. Chem. 1995; 60: 6895
• 14a Beletskaya IP, Sigeev AS, Peregudov AS, Petrovskii PV. Tetrahedron Lett. 2003; 44: 7039
• 14b Gujadhur RK, Venkataraman D. Tetrahedron Lett. 2003; 44: 81
• 14c Taniguchi N, Onami T. J. Org. Chem. 2004; 69: 915
• 14d Kumar S, Engman L. J. Org. Chem. 2006; 71: 5400
• 14e Alves D, Santos CG, Paixao MW, Soares LC, de Souza D, Rodrigues OE. D, Braga AL. Tetrahedron Lett. 2009; 50: 6635
• 14f Saha A, Saha D, Ranu BC. Org. Biomol. Chem. 2009; 7: 1652
• 14g Singh D, Alberto EE, Rodrigues OE. D, Braga AL. Green Chem. 2009; 11: 1521
• 14h Bhadra S, Saha A, Ranu BC. J. Org. Chem. 2010; 75: 4864
• 15a Correa A, Carril M, Bolm C. Angew. Chem. Int. Ed. 2008; 47: 2880
• 15b Wu WY, Wang JC, Tsai FY. Green Chem. 2009; 11: 326
• 15c Wang M, Ren K, Wang L. Adv. Synth. Catal. 2009; 351: 1586
• 15d Lee C.-F, Wu JR, Lin CH. Chem. Commun. 2009; 4450
• 16a Narayanaperumal S, Alberto EE, de Andrade FM, Lenardao EJ, Taube PS, Braga AL. Org. Biomol. Chem. 2009; 7: 4647
• 16b Wang L, Ren K, Wang M. Org. Biomol. Chem. 2009; 7: 4858
• 17a Bieber LW, de Sa AC. P. F, Menezes PH, Goncalves SM. C. Tetrahedron Lett. 2001; 42: 4597
• 17b Narayanaperumal S, Alberto EE, Gul K, Kawasoko CY, Dornelles L, Rodrigues OE. D, Braga AL. Tetrahedron 2011; 67: 4723
• 18a Charushin VS, Chupakhin ON In Metal-Free C–H Functionalization of Aromatic Compounds through the Action of Nucleophilic Reagents. Springer; New York: 2014
• 18b Sun C.-L, Shi Z.-J. Chem. Rev. 2014; 114: 9219
• 18c Wang D, Ge B, Li L, Shan J, Ding Y. J. Org. Chem. 2014; 79: 8607
• 18d Li L, Zhao Y.-L, Wang Q, Lin T, Liu Q. Org. Lett. 2015; 17: 370
• 19a Badsara SS, Liu Y.-C, Hsieh P.-A, Zeng J.-W, Lu S.-Y, Liu Y.-W, Lee C.-F. Chem. Commun. 2014; 50: 11374
• 19b Du B, Jin B, Sun P. Org. Lett. 2014; 16: 3032
• 19c Yuan J, Ma X, Yi H, Liu C, Lei A. Chem. Commun. 2014; 50: 14386
• 19d Xue Q, Xie J, Li H, Cheng Y, Zhu C. Chem. Commun. 2013; 49: 3700
• 19e Liou J.-C, Badsara SS, Huang Y.-T, Lee C.-F. RSC Adv. 2014; 4: 41237
• 19f Zeng J.-W, Liu Y.-C, Hsieh P.-A, Huang Y.-T, Yi C.-L, Badsara SS, Lee C.-F. Green Chem. 2014; 16: 2644
• 19g Liu D, Lei A. Chem. Asian J. 2015; 10: 806
• 20a Teicco M, Testaferri L, Bagnoli L, Marini F, Temperini A, Tomassini C, Santi C. Tetrahedron 2000; 56: 3255
• 20b Prasad CD, Balkrishna SJ, Kumar A, Bhakuni BS, Shrimali K, Biswas S, Kumar S. J. Org. Chem. 2013; 78: 1434
• 21 General Procedure for a Representative Example: Mesityl(phenyl)selane (3a) A Schlenk tube equipped with a magnetic stir bar was charged with diphenyl diselenide (0.5 mmol, 0.157 g), mesitylene (1.0 mL), and AcOOH (1.0 mmol), then heated at 120 °C in an oil bath under N₂ atmosphere. After stirring at this temperature for 24 h, the reaction mixture was cooled to r.t. and diluted with EtOAc (20 mL). The resulting solution was directly filtered through a pad of Celite then washed with EtOAc (20 mL) and concentrated to give the crude material which was then purified by column chromatography (SiO₂, hexane) to provide 3a as a yellow oil (248 mg, 94% yield). ¹H NMR (400 MHz, CDCl₃): δ = 2.30 (s, 3 H), 2.43 (s, 6 H), 6.99 (s, 2 H), 7.06–7.13 (m, 5 H) ppm. ¹³C NMR (100 MHz, CDCl₃): δ = 21.0, 24.2, 125.3, 128.4, 128.8, 128.9, 129.1, 133.4, 139.0, 143.6 ppm. ⁷⁷Se NMR (114.45 MHz, CDCl₃): δ = 286.3 ppm. HRMS (EI): m/z calcd for C₁₅H₁₆Se: 276.0417; found: 276.0407.