Palladium(II)-Catalyzed C–H Acylation with Arylglycine Derivatives

Abstract

A novel palladium(II)-catalyzed ortho acylation of arenes with arylglycines in the presence of Cu(OAc)₂ and K₂S₂O₈ to afford the benzophenones was developed. This direct C–H acylation is suitable for a broad range of substrates. The control experiments suggested a possible oxidative addition mechanism.

Key words

palladium(II)-catalyzed - ortho acylation - arylglycine - C–H activation - oxidative addition

• References and Notes


For recent reviews, see:
• 1a Mousseau JJ, Charette AB. Acc. Chem. Res. 2013; 46: 412
• 1b Kuhl N, Hopkinson MN, Wencel-Delord J, Glorius F. Angew. Chem. Int. Ed. 2012; 51: 10236
• 1c Bras JL, Muzart J. Chem. Rev. 2011; 111: 1170
• 1d McMurray L, O’Hara F, Gaunt MJ. Chem. Soc. Rev. 2011; 40: 1885
• 1e Baudoin O. Chem. Soc. Rev. 2011; 40: 4902
• 1f Wencel-Delord J, Dröge T, Kiu F, Glorius F. Chem. Soc. Rev. 2011; 40: 4740
• 1g Ackermann L. Chem. Rev. 2011; 111: 1315
• 1h Cho SH, Kim JY, Kwak J, Chang S. Chem. Soc. Rev. 2011; 40: 5068
• 1i Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
• 1j Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
• 1k Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
• 1l Li B.-J, Yang S.-D, Shi Z.-J. Synlett 2008; 949
• 1m Kakiuchi F, Kochi T. Synthesis 2008; 3013
• 2a McGrath NA, Brichacek M, Njardarson JT. J. Chem. Educ. 2010; 87: 1348
• 2b Gmouh S, Yang H, Vaultier M. Org. Lett. 2003; 5: 2219
• 2c Harrington PJ, Lodewijk E. Org. Process Res. Dev. 1997; 1: 72
• 2d Harvey G, Mader G. Collect. Czech. Chem. Commun. 1992; 57: 862
• 2e Sheldon RA. Chem. Ind. 1992; 903
• 2f Furniss BS, Hannaford AJ, Smith PW. G, Tatchell R. Vogel’s Textbook of Practical Organic Chemistry . Addison Wesley Longman; England: 1989. 5th ed. 1006
• 3a Heaney H In Comprehensive Organic Synthesis . Vol. 2. Trost BM, Fleming I. Pergamon Press; Oxford: 1991: 733
• 3b Olah GA. Friedel–Crafts Chemistry . Wiley; New York: 1973
• 3c Gore PH. Aromatic Ketone Synthesis . In Friedel–Crafts and Related Reactions . Olah GA. John Wiley; London: 1964. Part 1, Vol. 3 1
• 3d Gore PH. Chem. Rev. 1955; 55: 229

Selected references, see:
• 4a Sharghi H, Jokar M, Doroodmand MM, Khalifeh R. Adv. Synth. Catal. 2010; 352: 3031
• 4b de Noronha RG, Fernandes AC, Romao CC. Tetrahedron Lett. 2009; 50: 1407
• 4c Nishimoto Y, Babu SA, Yasuda M, Baba A. J. Org. Chem. 2008; 73: 9465
• 4d Gopalakrishnan M, Sureshkumar P, Kanagarajan V, Thanusu J. Catal. Commun. 2005; 6: 753
• 4e Hosseini Sarvari M, Sharghi H. J. Org. Chem. 2004; 69: 6953
• 4f Bartoli G, Bosco M, Marcantoni E, Massaceri M, Rinaldi S, Sambri L. Tetrahedron Lett. 2002; 43: 6331
• 4g Reetz MT, Giebel D. Angew. Chem. Int. Ed. 2000; 39: 2498

For selected examples of C–H acylation using aldehydes, see:
• 5a Jia X, Zhang S, Wang W, Luo F, Cheng J. Org. Lett. 2009; 11: 3120
• 5b Park J, Park E, Kim A, Lee Y, Chi K.-W, Kwak JH, Jung YH, Kim IS. Org. Lett. 2011; 13: 4390
• 5c Sharma S, Park E, Park J, Kim IS. Org. Lett. 2012; 14: 906
• 5d Sharma S, Park J, Park E, Kim A, Kim M, Kwak JH, Jung YH, Kim IS. Adv. Synth. Catal. 2013; 355: 332
• 5e Chan C.-W, Zhou Z, Chan AS. C, Yu W.-Y. Org. Lett. 2010; 12: 3926
• 5f Yang Y, Zhou B, Li Y. Adv. Synth. Catal. 2012; 354: 2916
• 5g Sharma S, Kim A, Park J, Kim M, Kwak JH, Jung YH, Park JS, Kim IS. Org. Biomol. Chem. 2013; 11: 7869
• 5h Baslé O, Bidange J, Shuai Q, Li C.-J. Adv. Synth. Catal. 2010; 352: 1145
• 5i Shin Y, Sharma S, Mishra NK, Han S, Paek J, Oh H, Ha J, Yoo H, Jung YH, Kim IS. Adv. Synth. Catal. 2015; 357: 594

For selected examples of C–H acylation using alcohols, see:
• 6a Xiao F, Shuai Q, Zhao F, Baslé O, Deng G, Li C.-J. Org. Lett. 2011; 13: 1614
• 6b Park J, Kim A, Sharma S, Kim M, Park E, Jeon Y, Lee Y, Kwak JH, Jung YH, Kim IS. Org. Biomol. Chem. 2013; 11: 2766
• 6c Kim M, Sharma S, Park J, Kim M, Choi Y, Jeon Y, Kwak JH, Kim IS. Tetrahedron 2013; 69: 6552
• 6d Sharma S, Kim M, Park J, Kim M, Kwak JH, Jung YH, Oh JS, Lee Y, Kim IS. Eur. J. Org. Chem. 2013; 6656

For selected examples of C–H acylation using α-oxocarboxylic acids, see:
• 7a Fang P, Li M, Ge H. J. Am. Chem. Soc. 2010; 132: 11898
• 7b Li M, Ge H. Org. Lett. 2010; 12: 3464
• 7c Wang H, Guo L.-N, Duan X.-H. Org. Lett. 2012; 14: 4358
• 7d Kim M, Park J, Sharma S, Kim A, Park E, Kwak JH, Jung YH, Kim IS. Chem. Commun. 2013; 49: 925
• 7e Park J, Kim M, Sharma S, Park E, Kim A, Lee SH, Kwak JH, Jung YH, Kim IS. Chem. Commun. 2013; 49: 1654
• 7f Sharma S, Kim A, Park E, Park J, Kim M, Kwak JH, Lee SH, Jung YH, Kim IS. Adv. Synth. Catal. 2013; 355: 667
• 7g Yu L, Li P, Wang L. Chem. Commun. 2013; 49: 2368
• 7h Li H, Li P, Zhao Q, Wang L. Chem. Commun. 2013; 49: 9170
• 7i Miao J, Ge H. Org. Lett. 2013; 15: 2930
• 7j Kim M, Mishra NK, Park J, Han S, Shin Y, Sharma S, Lee Y, Lee E.-K, Kwak JH, Kim IS. Chem. Commun. 2014; 50: 14249
• 8a Guin S, Rout SK, Banerjee A, Nandi S, Patel BK. Org. Lett. 2012; 14: 5294
• 8b Wu Y, Choy PY, Mao F, Kwong FY. Chem. Commun. 2013; 49: 689
• 9 Zhou W, Li H, Wang L. Org. Lett. 2012; 14: 4594
• 10 Lu J, Zhang H, Chen X, Liu H, Jiang Y, Fu H. Adv. Synth. Catal. 2013; 355: 529
• 11 Zhang Q, Yang F, Wu Y. Chem. Commun. 2013; 49: 6837
• 12 Han S, Sharma S, Park J, Kim M, Shin Y, Mishra NK, Bae JJ, Kwak JH, Jung YH, Kim IS. J. Org. Chem. 2014; 79: 275
• 13 Tlili A, Schranck J, Pospech J, Neumann H, Beller M. Angew. Chem. Int. Ed. 2013; 52: 6293
• 14 Wang R, An C.-H, Li Y, Zhao Y, Wang T, Li A. Tetrahedron Lett. 2015; 56: 2077
• 15a Ditrich K. Science of Synthesis . Vol. 25. Thieme; Stuttgart: 2007: 523
• 15b Srogl J, Voltrova S. Org. Lett. 2009; 11: 843
• 16a Murai S, Kakiuchi F, Sekine S, Tanaka Y, Kamatani A, Sonoda M, Chatani N. Nature (London, U.K.) 1993; 366: 529
• 16b Dupont J, Consorti CS, Spencer J. Chem. Rev. 2005; 105: 2527
• 17a Arnold PL, Sanford MS, Pearson SM. J. Am. Chem. Soc. 2009; 131: 13912
• 17b Baslé O, Bidange J, Shuai Q, Li C.-J. Adv. Synth. Catal. 2010; 352: 1145
• 17c Hickman AJ, Sanford MS. Nature (London, U.K.) 2012; 484: 177
• 17d Muñiz K. Angew. Chem. Int. Ed. 2009; 48: 9412
• 18 Synthesis of 3a–v A mixture of 1 (0.5 mmol), 2 (0.6 mmol), DMSO (5% H₂O aq, 5 mL), Pd(OAc)₂ (5 mol%), Cu(OAc)₂ (10 mol%), and K₂S₂O₈ (2 equiv) was stirred at 120 °C under Ar atmosphere for 24 h. The reaction mixture was washed with H₂O, and the aqueous phase was extracted with EtOAc (3×). The combined organic layer was washed with brine, dried over Na₂SO₄, and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography to give the corresponding products (3a–d,^7b 3f–k,^7b 3n–s ^7b). Compound 3e: yield 15%, white solid. ¹H NMR (500 MHz, CDCl₃): δ = 8.32 (d, J = 4.6 Hz, 1 H), 7.68 (m, 2 H), 7.52 (m, 2 H), 7.50 (m, 1 H), 7.41 (t, J = 7.2 Hz, 1 H), 7.25 (m, 2 H), 7.18 (m, 2 H), 7.0 (m, 1 H), 1.13 (s, 9 H). ¹³C NMR (125 MHz, CDCl₃): δ = 197.2, 158.0, 155.2, 148.5, 140.2, 136.8, 135.9, 131.5, 129.9, 129.3, 128.4, 127.8, 126,9, 121.3, 119.5, 114.1, 34.5, 15.8. HRMS: m/z calcd for C₂₂H₂₁NO: 315.1623; found: 315.1626.