Palladium-Catalyzed Decarboxylative Cross-Coupling of α-Oxocarboxylic Acids and Their Derivatives

Abstract

The development of palladium(II)-catalyzed decarboxylative cross-coupling of α-oxocarboxylic acids and their derivatives is summarized in this account. Acetanilides, 2-phenyl-pyridines, and benzoic acids were found to be suitable substrates for direct acylation through decarboxylative cross-coupling with α-oxo­carboxylic acids. Potassium aryl trifluoroborates were also transformed into ketones, amides, and esters with α-oxocarboxylic acids, oxamic acids, and oxalate monoesters, respectively, in modified catalytic systems.

1 Introduction

2 Palladium-Catalyzed Decarboxylative Cross-Coupling Through C–H Bond Functionalization

2.1 Direct ortho-Acylation of Acetanilides

2.2 Direct Acylation of 2-Phenylpyridines

2.3 Direct ortho-Acylation of Benzoic Acids

3 Transformation of Potassium Aryl Trifluoroborates into Ketones, Esters, and Amides

3.1 Formation of Aryl Ketones from Potassium Aryl Trifluoroborates

3.2 Preparation of Aryl Amides and Esters from Potassium Aryl Trifluoroborates

3.3 Mechanistic Studies

4 Conclusions and Outlook

Key words

palladium - catalysis - carboxylic acids - decarboxylation - carbonylation - cross-coupling

• References


For recent reviews, see:
• 1a Baudoin O. Angew. Chem. Int. Ed. 2007; 46: 1373
• 1b Gooßen LJ, Gooßen K, Rodríguez N, Blanchot M, Linder C, Zimmermann B. Pure Appl. Chem. 2008; 80: 1725
• 1c Gooßen LJ, Rodríguez N, Gooßen K. Angew. Chem. Int. Ed. 2008; 47: 3100
• 1d Gooßen LJ, Collet F, Gooßen K. Isr. J. Chem. 2010; 50: 617
• 1e Bonesi SM, Fagnoni M. Chem. Eur. J. 2010; 16: 13572
• 1f Rodríguez N, Gooßen LJ. Chem. Soc. Rev. 2011; 40: 5030
• 1g Shang R, Liu L. Sci. China: Chem. 2011; 54: 1670
• 1h Cornella J, Larrosa I. Synthesis 2012; 44: 653
• 2 Myers AG, Tanaka D, Mannion R. J. Am. Chem. Soc. 2002; 124: 11250
• 3a Gooßen LJ, Deng GJ, Levy LM. Science 2006; 313: 662
• 3b Gooßen LJ, Rodríguez N, Melzer B, Linder C, Deng GJ, Levy LM. J. Am. Chem. Soc. 2007; 129: 4824
• 4a Voutchkova A, Coplin A, Leadbeater NE, Crabtree RH. Chem. Commun. 2008; 6312
• 4b Hu P, Kan J, Su W.-P, Hong M.-C. Org. Lett. 2009; 11: 2341
• 4c Yu W.-Y, Sit WN, Zhou Z, Chan AS.-C. Org. Lett. 2009; 11: 3174
• 4d Wei Y, Kan J, Wang M, Su W.-P, Hong M.-C. Org. Lett. 2009; 11: 3346
• 4e Cornella J, Lu PF, Larrosa I. Org. Lett. 2009; 11: 5506
• 4f Wang CY, Piel I, Glorius F. J. Am. Chem. Soc. 2009; 131: 4194
• 4g Zhang FZ, Greaney MF. Angew. Chem. Int. Ed. 2010; 49: 2768
• 4h Zhou J, Hu P, Zhang M, Huang S, Wang M, Su W. Chem. Eur. J. 2010; 16: 5876
• 4i Xie K, Yang Z, Zhou X, Li X, Wang S, Tan Z, An X, Guo C.-C. Org. Lett. 2010; 12: 1564
• 4j Zhao H.-Q, Wei Y, Xu J, Kan J, Su W.-P, Hong M.-C. J. Org. Chem. 2011; 76: 882
• 4k Hu P, Zhang M, Jie X.-M, Su W.-P. Angew. Chem. Int. Ed. 2012; 51: 227
• 4l Hu P, Shang Y.-P, Su W.-P. Angew. Chem. Int. Ed. 2012; 51: 5945
• 5a Minisci F, Citterio A, Giordano C. Acc. Chem. Res. 1983; 16: 27
• 5b Minisci F, Vismara E, Fontana F. Heterocycles 1989; 28: 489
• 5c Fontana F, Minisci F, Barbosa MC. N, Vismara E. J. Org. Chem. 1991; 56: 2866
• 5d Chatgilialoglu C, Crich D, Komatsu M, Ryu I. Chem. Rev. 1999; 99: 1991
• 5e Punta C, Minisci F. Trends Heterocycl. Chem. 2008; 13: 1
• 6a Gooßen LJ, Rudolphi F, Oppel C, Rodríguez N. Angew. Chem. Int. Ed. 2008; 47: 3043
• 6b Gooßen LJ, Zimmermann B, Knauber T. Angew. Chem. Int. Ed. 2008; 47: 7103
• 6c Gooßen LJ, Zimmermann B, Linder C, Rodríguez N, Lange PP, Hartung J. Adv. Synth. Catal. 2009; 351: 2667
• 7a Kalyani D, Deprez NR, Desai LV, Sanford MS. J. Am. Chem. Soc. 2005; 127: 7330
• 7b Daugulis O, Zaitsev VG. Angew. Chem. Int. Ed. 2005; 44: 4046
• 7c Wan X.-B, Ma Z.-X, Li B.-J, Zhang K, Cao S.-K, Zhang S.-W, Shi Z.-J. J. Am. Chem. Soc. 2006; 128: 7416
• 7d Yang S.-D, Li B.-J, Wan X.-B, Shi Z.-J. J. Am. Chem. Soc. 2007; 129: 6066
• 7e Shi Z.-J, Li B.-J, Wan X.-B, Cheng J, Fang Z, Cao B, Qin C.-M, Wang Y. Angew. Chem. Int. Ed. 2007; 46: 5554
• 7f Houlden CE, Bailey CD, Ford JG, Gagné MR, Lloyd-Jones GC, Booker-Milburn KI. J. Am. Chem. Soc. 2008; 130: 10066
• 7g Li B.-J, Tian S.-L, Fang Z, Shi Z.-J. Angew. Chem. Int. Ed. 2008; 47: 1115
• 7h Wang G.-W, Yuan T.-T, Wu X.-L. J. Org. Chem. 2008; 73: 4717
• 7i Tobisu M, Ano Y, Chatani N. Org. Lett. 2009; 11: 3250
• 7j Giri R, Lam JK, Yu J.-Q. J. Am. Chem. Soc. 2010; 132: 686
• 7k Bedford RB, Haddow MF, Mitchell CJ, Webster RL. Angew. Chem. Int. Ed. 2011; 50: 5524
• 8a Nishikata T, Abela AR, Huang S.-L, Lipshutz BH. J. Am. Chem. Soc. 2010; 132: 4978
• 8b Nishikata T, Lipshutz BH. Org. Lett. 2010; 12: 1972
• 9 Fang P, Li M.-Z, Ge H.-B. J. Am. Chem. Soc. 2010; 132: 11898
• 10 Yamashita M, Hirano K, Satoh T, Miura M. Chem. Lett. 2010; 39: 68
• 11a Dick AR, Hull KL, Sanford MS. J. Am. Chem. Soc. 2004; 126: 2300
• 11b Shabashov D, Daugulis O. Org. Lett. 2005; 7: 3657
• 11c Hull KL, Anani WQ, Sanford MS. J. Am. Chem. Soc. 2006; 128: 7134
• 11d Chen X, Goodhue CE, Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 12634
• 11e Hull KL, Lanni EL, Sanford MS. J. Am. Chem. Soc. 2006; 128: 14047
• 11f Hull KL, Sanford MS. J. Am. Chem. Soc. 2007; 129: 11904
• 11g Yu W.-Y, Sit WN, Lai K.-M, Zhou Z.-Y, Chan AS. C. J. Am. Chem. Soc. 2008; 130: 3304
• 11h Deprez NR, Sanford MS. J. Am. Chem. Soc. 2009; 131: 11234
• 11i Xiao F.-H, Shuai Q, Zhao F, Basle O, Deng G.-J, Li C.-J. Org. Lett. 2011; 13: 1614
• 11j Zhou W, Li H.-J, Wang L. Org. Lett. 2012; 14: 4594
• 11k Powers DC, Geibel MA. L, Klein JE. M. N, Ritter T. J. Am. Chem. Soc. 2009; 131: 17050 ; see also ref. 4a
• 12 Li M.-Z, Ge H.-B. Org. Lett. 2010; 12: 3464
• 13a Sexton WA, Templeman WG. Nature 1948; 141: 974
• 13b Evans D, Cracknell ME, Saunders JC, Smith CE, Williamson WR. N, Dawson W, Sweatman WJ. F. J. Med. Chem. 1987; 30: 1321
• 13c Gapinski DM, Mallett BE, Froelich LL, Jackson WT. J. Med. Chem. 1990; 33: 2798
• 13d Wyss DF, Arasappan A, Senior MM, Wang Y.-S, Beyer BM, Njoroge FG, McCoy MA. J. Med. Chem. 2004; 47: 2486
• 13e Gobec S, Brožič P, Rižner TL. Bioorg. Med. Chem. Lett. 2005; 15: 5170
• 14a Fieser LF, Hershberg EB. J. Am. Chem. Soc. 1937; 59: 2331
• 14b Newman MS, Muth CW. J. Am. Chem. Soc. 1950; 72: 5191
• 14c LaBudde JA, Heidelberger C. J. Am. Chem. Soc. 1958; 80: 1225
• 14d Seo S, Slater M, Greaney MF. Org. Lett. 2012; 14: 2650
• 15a Newman MS, Scheurer PG. J. Am. Chem. Soc. 1956; 78: 5004
• 15b Reinheckel HA, Haage K. Angew. Chem. Int. Ed. 1966; 5: 511
• 15c Watson AF, Liu J.-F, Bennaceur K, Drummond CJ, Endicott JA, Golding BT, Griffin RJ, Haggerty K, Lu X.-H, McDonnell JM, Newell DR, Noble ME. M, Revill CH, Riedinger C, Xu Q, Zhao Y, Lunec J, Hardcastle IR. Bioorg. Med. Chem. Lett. 2011; 21: 5916
• 15d Wang X, Li J.-Z, Zhao N, Wan X.-B. Org. Lett. 2011; 13: 709
• 15e Yu H.-B, Xiao Y, Guo H.-Y. Org. Lett. 2012; 14: 2014
• 16a Giri R, Maugel N, Li J.-J, Wang D.-H, Breazzano SP, Saunders LB, Yu J.-Q. J. Am. Chem. Soc. 2007; 129: 3510
• 16b Chiong HA, Pham Q.-N, Daugulis O. J. Am. Chem. Soc. 2007; 129: 9879
• 16c Mei T.-S, Giri R, Maugel N, Yu J.-Q. Angew. Chem. Int. Ed. 2008; 47: 5215
• 16d Giri R, Yu J.-Q. J. Am. Chem. Soc. 2008; 130: 14082
• 16e Wang D.-H, Mei T.-S, Yu J.-Q. J. Am. Chem. Soc. 2008; 130: 17676
• 17 Miao J.-M, Ge H.-B. Org. Lett. 2013; 15: 2930
• 18 Ukita T, Nakamura Y, Kubo A, Yamamoto Y, Moritani Y, Saruta K, Higashijima T, Kotera J, Takagi M, Kikkawa K, Omori K. J. Med. Chem. 2001; 44: 2204
• 19 Wang H, Guo L.-N, Duan X.-H. Org. Lett. 2012; 14: 4358
• 20a Kim M, Park J, Sharma S, Kim A, Park E, Kwak JH, Jung YH, Kim IS. Chem. Commun. 2013; 49: 925
• 20b Yang Z.-Y, Chen X, Liu J.-D, Gui Q.-W, Xie K, Li M.-M, Tan Z. Chem. Commun. 2013; 49: 1560
• 21 Park J, Kim M, Sharma S, Park E, Kim A, Lee SH, Kwak JH, Jung YH, Kim IS. Chem. Commun. 2013; 49: 1654
• 22 Sharma S, Kim A, Park E, Park J, Kim M, Kwak JH, Lee SH, Jung YH, Kim IS. Adv. Synth. Catal. 2013; 355: 667
• 23 Pan C.-D, Jin H.-M, Liu X, Cheng Y.-X, Zhu C.-J. Chem. Commun. 2013; 49: 2933

For recent reviews, see:
• 24a Bellina F, Carpita A, Rossi R. Synthesis 2004; 2419
• 24b Baudoin O. Eur. J. Org. Chem. 2005; 4223
• 24c Phan NT. S, Van Der Sluys M, Jones CW. Adv. Synth. Catal. 2006; 348: 609
• 24d Miyaura N. Bull. Chem. Soc. Jpn. 2008; 81: 1535
• 24e Tobisu M, Chatani N. Angew. Chem. Int. Ed. 2009; 48: 3565
• 24f Molander GA, Canturk B. Angew. Chem. Int. Ed. 2009; 48: 9240
• 24g Miyaura N. Synlett 2009; 2039
• 24h Knappke CE. I, von Wangelin AJ. Angew. Chem. Int. Ed. 2010; 49: 3568
• 24i Suzuki A. Angew. Chem. Int. Ed. 2011; 50: 6722
• 24j Heravi MM, Hashemi E. Tetrahedron 2012; 68: 9145
• 24k Blangetti M, Rosso H, Prandi C, Deagostino A, Venturello P. Molecules 2013; 18: 1188
• 25 Molander GA, Ellis N. Acc. Chem. Res. 2007; 40: 275
• 26 Li M.-Z, Wang C, Ge H.-B. Org. Lett. 2011; 13: 2062
• 27 Shang R, Fu Y, Li JB, Zhang SL, Guo QX, Liu L. J. Am. Chem. Soc. 2009; 131: 5738
• 28 Li M.-Z, Wang C, Fang P, Ge H.-B. Chem. Commun. 2011; 47: 6587
• 29a Dick AR, Kampf J, Sanford MS. J. Am. Chem. Soc. 2005; 127: 12790
• 29b Tong X, Beller M, Tse MK. J. Am. Chem. Soc. 2007; 129: 4906
• 29c Welbes LL, Lyons TW, Cychosz KA, Sanford MS. J. Am. Chem. Soc. 2007; 129: 5836
• 29d Sibbald PA, Rosewall CF, Swartz RD, Michael FE. J. Am. Chem. Soc. 2009; 131: 15945
• 29e Wang G.-W, Yuan T.-T. J. Org. Chem. 2010; 75: 476
• 29f Lysons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
• 29g Neufeldt SR, Sanford MS. Acc. Chem. Res. 2012; 45: 936