tert-Butoxide-Mediated Arylation of 1-Acetylindolin-3-ones with Diaryliodonium Salts

Abstract

A procedure for the 2-arylations of indolinone derivatives with diaryliodonium salts mediated by potassium tert-butoxide is developed. Various monoarylated indolinone derivatives are readily obtained in 24–70% yield via this method. The alkylation of monoarylated indolinone derivatives with allyl bromide or benzyl bromide affords the corresponding 2,3-disubstituted products in 60% and 70% yield, respectively.

Key words

arylation - diaryliodonium salts - metal-free - indolinone - ­alkylation

• References and Notes

• 1a Yanagisawa S, Ueda K, Taniguchi T, Itami K. Org. Lett. 2008; 10: 4673
• 1b Liu W, Cao H, Zhang H, Zhang H, Chung KH, He C, Wang H, Kwong FY, Lei A. J. Am. Chem. Soc. 2010; 132: 16737
• 1c Shirakawa E, Itoh K, Higashino T, Hayashi T. J. Am. Chem. Soc. 2010; 132: 15537
• 1d Sun CL, Li H, Yu DG, Yu M, Zhou X, Lu XY, Huang K, Zheng SF, Li BJ, Shi ZJ. Nat. Chem. 2010; 2: 1044
• 2a Zhdankin VV, Stang PJ. Chem. Rev. 2002; 102: 2523
• 2b Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
• 2c Merritt EA, Olofsson B. Angew. Chem. Int. Ed. 2009; 48: 9052
• 2d Silva LF, Olofsson B. Nat. Prod. Rep. 2011; 28: 1722
• 2e Yusubov MS, Maskaev AV, Zhdankin VV. ARKIVOC 2011; (i): 370
• 2f Yusubov MS, Zhdankin VV. Curr. Org. Synth. 2012; 9: 247
• 3a Grushin VV, Kantor MM, Tolstaya TP, Shcherbina TM. Russ. Chem. Bull. 1984; 33: 2130
• 3b Kita Y, Morimoto K, Ito M, Ogawa C, Goto A, Dohi T. J. Am. Chem. Soc. 2009; 131: 1668
• 3c Dohi T, Ito M, Yanaoka N, Morimoto K, Fujioka H, Kita Y. Angew. Chem. Int. Ed. 2010; 49: 3334
• 3d Yamaoka N, Sumida K, Itani I, Kubo H, Ohnishi Y, Sekiguchi S, Dohi T, Kita Y. Chem. Eur. J. 2013; 19: 15004
• 3e Ackermann L, Dell’Acqua M, Fenner S, Vicente R, Sandmann R. Org. Lett. 2011; 13: 2358
• 3f Wen J, Zhang R.-Y, Chen S.-Y, Zhang J, Yu X.-Q. J. Org. Chem. 2012; 77: 766
• 3g Castro S, Fernández JJ, Vicente R, Fañanás FJ, Rodríguez F. Chem. Commun. 2012; 48: 9089
• 3h Jalalian N, Ishikawa EE, Siva LF. Jr, Olofsson B. Org. Lett. 2011; 13: 1552
• 3i Petersen TB, Khan R, Olofsson B. Org. Lett. 2011; 13: 3462
• 3j Jalalian N, Petersen TB, Olofsson B. Chem. Eur. J. 2012; 18: 14140
• 3k Ghosh R, Lindstedt E, Jalalian N, Olofsson B. ChemistryOpen 2014; 3: 54
• 3l Ghosh R, Olofsson B. Org. Lett. 2014; 16: 1830
• 3m Carroll MA, Wood RA. Tetrahedron 2007; 63: 11349
• 3n Li J, Liu L. RSC Adv. 2012; 2: 10485
• 3o Umierski N, Manolikakes G. Org. Lett. 2013; 15: 188
• 3p Ozanne-Beaudenon A, Quideau S. Angew. Chem. Int. Ed. 2005; 44: 7065
• 3q Landge KP, Jang KS, Lee SY, Chi DY. J. Org. Chem. 2012; 77: 5705
• 4a Zhou T, Chen Z.-C. Synth. Commun. 2002; 32: 903
• 4b Deprez NR, Kalyani D, Krause A, Sanford MS. J. Am. Chem. Soc. 2006; 128: 4972
• 4c Phipps RJ, Grimster NP, Gaunt MJ. J. Am. Chem. Soc. 2008; 130: 8172
• 4d Guo F, Wang L, Wang P, Yu J, Han J. Asian J. Org. Chem. 2012; 1: 218
• 4e Guo F, Han J, Mao S, Li J, Geng X, Yu J, Wang L. RSC Adv. 2013; 3: 6267
• 5a Beringer FM, Forgione PS, Yudis MD. Tetrahedron 1960; 8: 49
• 5b Beringer FM, Galton SA, Huang SJ. J. Am. Chem. Soc. 1962; 84: 2819
• 5c Beringer FM, Forgione PS. Tetrahedron 1963; 19: 739
• 5d Beringer FM, Daniel WJ, Galton SA, Rubin G. J. Org. Chem. 1966; 31: 4315
• 5e Ryan JH, Stang PJ. Tetrahedron Lett. 1997; 38: 5061
• 6 Chai Z, Wang B, Chen J.-N, Yang G. Adv. Synth. Catal. 2014; 356: 2714
• 7 Monastyrskyi A, Namelikonda NK, Manetsch R. J. Org. Chem. 2015; 80: 2513
• 8 Mao S, Geng X, Yang Y, Qian X, Wu S, Han J, Wang L. RSC Adv. 2015; 5: 36390
• 9a Kawasaki T, Tang C.-Y, Nakanishi H, Hirai S, Ohshita T, Tanizawa M, Himori M, Satoh H, Sakamoto M, Miura K, Nakano F. J. Chem. Soc., Perkin Trans. 1 1999; 327
• 9b Mérour J.-Y, Gadonneix P, Malapel-Andrieu B, Desarbre E. Tetrahedron 2001; 57: 1995
• 9c Higuchi K, Sato Y, Kojima S, Tsuchimochi M, Sugiura K, Hatori M, Kawasaki T. Tetrahedron 2010; 66: 1236
• 9d Liu Y.-Z, Zhang J, Xu P.-F, Luo Y.-C. J. Org. Chem. 2011; 76: 7551
• 9e Ni Q, Song X, Raabe G, Enders D. Chem. Asian J. 2014; 9: 1535
• 9f Chen T.-G, Fang P, Hou X.-L, Dai L.-X. Synthesis 2015; 47: 134
• 9g Mahajan S, Chauhan P, Loh CC. J, Uzungelis S, Raabe G, Enders D. Synthesis 2015; 47: 1024
• 10a Chien C.-S, Suzuki T, Kawasaki T, Sakamoto M. Chem. Pharm. Bull. 1984; 32: 3945
• 10b Chien C.-S, Takanami T, Kawasaki TT, Sakamoto M. Chem. Pharm. Bull. 1985; 33: 1843
• 10c Chien C.-S, Hasegawa A, Kawasaki T, Sakamoto M. Chem. Pharm. Bull. 1986; 34: 1493
• 10d Kawasaki T, Masuda K, Baba Y, Terashima R, Takada K, Sakamoto M. J. Chem. Soc., Perkin Trans. 1 1996; 729
• 10e Bourlot AS, Desarbre E, Mérour JY. Synthesis 1994; 411
• 11 Mérour J.-Y, Chichereau L, Finet J.-P. Tetrahedron Lett. 1992; 33: 3867
• 12 Compounds 3ba−ja; General Procedure Indolinone 1 (0.2 mmol, 1 equiv) and t-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv) were added to a Schlenk tube. THF (2 mL) was added using a syringe and the mixture was stirred for 15 min. Next, iodonium salt 2 (0.0860 g, 0.2 mmol, 1.0 equiv) was added and the mixture was stirred at 30 °C for 10 h. After cooling to r.t., the solvent was removed in vacuo and the residue was purified over silica gel (EtOAc–hexane) to afford the desired product. Analytical data for representative sample 3aa is provided below. 1-Acetyl-2-phenylindolin-3-one (3aa) Yield: 29.2 mg (58%); white solid; mp 125–128 °C. ¹H NMR (300 MHz, CDCl₃): δ = 8.67 (d, J = 7.8 Hz, 1 H), 7.80–7.65 (m, 2 H), 7.44–7.32 (m, 3 H), 7.30–7.22 (m, 3 H), 5.19 (s, 1 H), 2.05 (s, 3 H). ¹³C NMR (75 MHz, CDCl₃): δ = 195.2, 169.5, 154.1, 137.8, 134.8, 129.7, 129.0, 126.0, 125.0, 123.0, 118.7, 107.9, 69.9, 24.8. HRMS (ESI): m/z [M + H]⁺ calcd for C₁₆H₁₃NO₂: 252.1025; found: 252.1025.