Synlett 2013; 24(11): 1322-1339
DOI: 10.1055/s-0033-1338943
account
© Georg Thieme Verlag Stuttgart · New York

An Expedition Through the Last Decade of Heterocycle Construction by Using Palladium, Iron, Copper, or Iodine/tert-Butyl Hydroperoxide

Lingfeng Gao
Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Soft Matter Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, P. R. of China   Fax: +86(551)3603185   Email: zwang3@ustc.edu.cn
,
Shunshun Xiong
Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Soft Matter Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, P. R. of China   Fax: +86(551)3603185   Email: zwang3@ustc.edu.cn
,
Changfeng Wan
Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Soft Matter Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, P. R. of China   Fax: +86(551)3603185   Email: zwang3@ustc.edu.cn
,
Zhiyong Wang*
Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Soft Matter Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, P. R. of China   Fax: +86(551)3603185   Email: zwang3@ustc.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 08 February 2013

Accepted after revision: 12 April 2013

Publication Date:
13 June 2013 (online)


Abstract

Over the past decade, our group has developed a series of synthetic methods for the preparation of heterocycles by using two different approaches: transition-metal-catalyzed cyclization and ­iodine/oxidant-catalyzed oxidative cyclization. Transition-metal salts of palladium or iron and nanoparticulate copper(II) oxide have been used as catalysts for the synthesis of heterocyclic compounds. Palladium-catalyzed Wacker-type oxidative heterocyclic cyclization, iron-catalyzed benzylation and tandem dehydration annulation, and nanoparticulate copper(II) oxide-catalyzed heterogeneous oxidative cyclizations have been developed in our laboratory. For iodine-catalyzed reactions, we have developed an oxidative tandem cyclization, an oxidative decarboxylative coupling cyclization, a direct Mannich-like reaction, and an oxidative amination catalyzed by diiodine and tert-butyl hydroperoxide under mild condition. These methods have enriched the range of synthetic strategies available for the construction of heterocyclic skeletons and they have potential applications in the fields of medicinal chemistry and materials science.

1 Introduction

2 Transition Metal-Catalyzed Heterocyclic Cyclization

2.1 Palladium-Catalyzed Wacker-Type Oxidative Heterocyclic Cyclization

2.1.1 Synthesis of 2-Methyl-2H-chromen-3(4H)-ones

2.1.2 Synthesis of 2-Methylquinolines

2.1.3 Synthesis of Pyrroles from Amino Acids

2.2 Lewis acid Iron(III) Chloride Catalyzed Intermolecular Cyclization Through Benzylation

2.2.1 Preparation of Functionalized 4H-Chromenes

2.2.2 Preparation of 3-Quinolinecarboxylic Acid Esters

2.2.3 Preparation of Highly Functionalized 2,3-Dihydro-1H-pyrroles

2.3 Syntheses of Quinazolines and 2-Aryldihydrobenzofurans Catalyzed by Nanoparticulate Copper(II) Oxide or Copper(I) Chloride

2.3.1 Synthesis of Quinazolines in the Presence of Copper(II) Oxide Nanoparticles

2.3.2 One-Pot Synthesis of 2-Aryl-2,3-dihydro-1-benzofurans Catalyzed by Copper(I) Chloride

3 Diiodine/tert-Butyl Hydroperoxide-Catalyzed Heterocyclic Cyclization

3.2 Synthesis of Highly Functionalized Oxazoles

3.3 Synthesis of 2-Phenylquinazoline by sp3 C–H Functionalization with Diiodine/tert-Butyl Hydroperoxide

3.4 Synthesis of Quinazolines Through Amination of Primary a-Amino Acids or sp3 C–H Bonds Adjacent to Nitrogen or Oxygen Atoms

3.5 Synthesis of Benzofurans and Naphthofurans

4 Conclusion

 
  • References

  • 1 Gilchrist TL. J. Chem. Soc., Perkin Trans. 1 1999; 2849
  • 2 Gonzalez MC, Serrano A, Zafra-Polo MC, Cortes D, Rao KS. J. Nat. Prod. 1995; 58: 1278
    • 3a Handbook of C–H Transformations: Applications in Organic Synthesis. Dyker G. Wiley-VCH; Weinheim: 2005
    • 3b Clara IH, Xiao QY, Zhi PL, Chao JL. Chem. Rev. 2007; 107: 2546
    • 3c Chang LS, Bi JL, Zhang JS. Chem. Rev. 2011; 111: 1293
    • 3d Chao L, Hua Z, Wei S, Wen AL. Chem. Rev. 2011; 111: 1780
    • 4a Viktor K. Mark W. H. 2002; 102: 61
    • 4b Itaru N, Yoshinori Y. Chem. Rev. 2004; 104: 2127
    • 4c Martins MA. P, Frizzo CP, Moreira DN, Buriol L, Machado P. Chem. Rev. 2009; 109: 4140
    • 4d Katritzky AR, Rachwal S. Chem. Rev. 2011; 111: 7063
    • 4e Maükosza M, Wojciechowski K. Chem. Rev. 2004; 104: 2631
    • 5a Tsuji J. Palladium Reagents and Catalysts . Wiley; Chichester: 2004: 27
    • 5b Henry PM In Handbook of Organopalladium Chemistry for Organic Synthesis . Negishi E. Wiley; New York: 2002. Chap. V3.1.1, 2119
    • 5c Hosokawa T, Murahashi SI In Handbook of Organopalladium Chemistry for Organic Synthesis . Negishi E. Wiley; New York: 2002. Chap. V3.1.2 2141
    • 5d Zeni G, Larock RC. Chem. Rev. 2006; 106: 4644
    • 5e Zeni G, Larock RC. Chem. Rev. 2004; 104: 2285
    • 5f Stoltz BM. Chem. Lett. 2004; 33: 362
    • 5g Minatti A, Muñiz K. Chem. Soc. Rev. 2007; 36: 1142
    • 5h Zhang ZH, Pan CF, Wang ZY. Chem. Commun. (Cambridge) 2007; 4686
    • 5i Zhang ZH, Tan JJ, Wang ZY. Org. Lett. 2008; 10: 173
    • 5j Zhang ZH, Zhang JT, Tan JJ, Wang ZY. J. Org. Chem. 2008; 73: 5180
    • 6a Ishikawa T, Oku Y, Tanaka T, Kumamoto T. Tetrahedron Lett. 1999; 40: 3777
    • 6b Xu Z.-Q, Buckheit RW. Jr, Stup TL, Flavin MT, Khilevich A, Rizzo JD, Lin L, Zembower DE. Bioorg. Med. Chem. Lett. 1998; 8: 2179
    • 6c Flavin MT, Rizzo JD, Khilevich A, Kucherenko A, Sheinkman AK, Vilaychack V, Lin L, Chen W, Greenwood EM, Pengsuparp T, Pezzuto JM, Hughes SH, Flavin TM, Cibulski M, Boulanger WA, Shone RL, Xu Z.-Q. J. Med. Chem. 1996; 39: 1303
    • 6d Ishikawa T. Heterocycles 2000; 53: 453
    • 6e Yu DL, Suzuki M, Xie L, Morris-Natschke SL, Lee K.-H. Med. Res. Rev. 2003; 23: 322
    • 7a Ishikawa T, Oku Y, Kotake KI, Ishii H. J. Org. Chem. 1996; 61: 6484
    • 7b Biddle MM, Lin M, Scheidt KA. J. Am. Chem. Soc. 2007; 129: 3830
    • 7c Cui DM, Kawamura M, Shimada S, Hayashi T, Tanaka M. Tetrahedron Lett. 2003; 44: 4007
    • 7d Hwu JR, Wein YS, Leu YJ. J. Org. Chem. 1996; 61: 1493
    • 7e Bisai A, Chandrasekhar M, Singh VK. Tetrahedron Lett. 2002; 43: 8355
    • 7f Skouta R, Li CJ. Angew. Chem. Int. Ed. 2007; 46: 1117
  • 8 Michael JP. Nat. Prod. Rep. 2007; 24: 223
    • 9a Balasubramanian M, Keay JG In Comprehensive Heterocyclic Chemistry II . Vol. 5. Katritzky AR, Rees CW, Scriven EF. V. Pergamon; Oxford: 1996: 245
    • 9b Chen YL, Fang KC, Sheu JY, Hsu SL, Tzeng C. J. Med. Chem. 2001; 44: 2374
    • 9c Roma G, Braccio MD, Grossi G, Mattioli F, Ghia M. Eur. J. Med. Chem. 2000; 35: 1021
    • 9d Maguire MP, Sheets KR, McVety K, Spada AP, Zilberstein A. J. Med. Chem. 1994; 37: 2129
    • 9e Bilker O, Lindo V, Panico M, Etiene AE, Paxton T, Dell A, Rogers M, Sinden RE, Morris HR. Nature (London) 1998; 289
    • 10a The Chemistry of Heterocyclic Compounds . Vol. 48, Part 2. Jones AR. Wiley Interscience; New York: 1992
    • 10b Fürstner A. Angew. Chem. Int. Ed. 2003; 42: 3582
    • 10c Bando T, Sugiyama H. Acc. Chem. Res. 2006; 39: 935
    • 11a Bolm C, Legros J, Le Paih J. Zani L. 2004; 104: 6217
    • 11b Enthaler S, Junge K, Beller M. Angew. Chem. Int. Ed. 2008; 47: 3317
    • 11c Correa A, Mancheno OG, Bolm C. Chem. Soc. Rev. 2008; 37: 1108
    • 11d Sherry BD, Furstner A. Acc. Chem. Res. 2008; 41: 1500
    • 11e Gaillard S, Renaud JL. ChemSusChem. 2008; 1: 505
    • 11f Czaplik WM, Mayer MJ, Cvengroš J, von Wangelin AJ. ChemSusChem. 2009; 2: 396
    • 11g Fan JM, Wang ZY. Chem. Commun. (Cambridge) 2008; 5381
    • 11h Fan JM, Wan CF. Sun G. J, Wang ZY. J. Org. Chem. 2008; 73: 8608
    • 11i Fan JM, Gao LF, Wang ZY. Chem. Commun. (Cambridge) 2009; 5021
    • 12a Iovel I, Mertins K, Kischel J, Zapf A, Beller M. Angew. Chem. Int. Ed. 2005; 44: 3913
    • 12b Yasuda M, Somyo T, Baba A. Angew. Chem. Int. Ed. 2006; 45: 793
    • 12c Motokura K, Fujita N, Mori K, Mizugaki T, Ebitani K, Kaneda K. Angew. Chem. Int. Ed. 2006; 45: 2605
    • 12d Kischel J, Mertins K, Michalik D, Zapf A, Beller M. Adv. Synth. Catal. 2007; 349: 865
    • 12e Rueping M, Nachtsheim BJ, Kuenkel A. Org. Lett. 2007; 9: 825
    • 13a Appel B, Saleh NN. R, Langer P. Chem. Eur. J. 2006; 12: 1221
    • 13b Nising CF, Ohnemüller UK, Bräse S. Angew. Chem. Int. Ed. 2006; 45: 307
    • 14a Corey EJ, Wu LI. J. Am. Chem. Soc. 1993; 115: 9327
    • 14b Wang JL, Liu DX, Zhang Z.-J, Shan SM, Han XB, Srinivasula SM, Croce CM, Alnemri ES, Huang ZW. Proc. Natl. Acad. Sci. U. S. A. 2000; 97: 7124
    • 15a Hegedus LS, McKearin JM. J. Am. Chem. Soc. 1982; 104: 2444
    • 15b Ichikawa J, Fujiwara M, Wada Y, Okauchi T, Minami T. Chem. Commun. (Cambridge) 2000; 1887
    • 15c Hamaguchi H, Kosaka S, Ohno H, Tanaka T. Angew. Chem. Int. Ed. 2005; 44: 1513
    • 15d Ma SM, Yu F, Li J, Gao WZ. Chem. Eur. J. 2007; 13: 247
    • 15e Carney JM, Donoghue PJ, Wuest WM, Wiest O, Helquist P. Org. Lett. 2008; 10: 3903
    • 15f Brawn RA, Panek JS. Org. Lett. 2009; 11: 473
    • 15g Brichacek M, Njardarson JT. Org. Biomol. Chem. 2009; 7: 1761
    • 16a Lucet D, Gallo TL, Mioskowski C. Angew. Chem. Int. Ed. 1998; 37: 2580
    • 16b Wu J, Hou X.-L, Dai L.-X. J. Chem. Soc., Perkin Trans. 1 2001; 1314
    • 16c Luo ZB, Wu JY, Hou X.-L, Dai L.-X. Org. Biomol. Chem. 2007; 5: 3428
    • 16d Wu JY, Luo Z.-B, Dai L.-X, Hou X.-L. J. Org. Chem. 2008; 73: 9137
    • 16e Chen DD, Hou X.-L, Dai L.-X. J. Org. Chem. 2008; 73: 5578
  • 17 See refs. 15a–e and 15g.
  • 18 Wender PA, Strand D. J. Am. Chem. Soc. 2009; 7528
    • 19a Mhaske SB, Argade NP. Tetrahedron 2006; 62: 9787
    • 19b Michael JP. Nat. Prod. Rep. 2008; 25: 166
    • 19c Zhang JT, Yu CM, Wang SJ, Wan CF, Wang ZY. Chem. Commun. (Cambridge) 2010; 46: 5244
    • 19d Zhang JT, Zhu DP, Yu CM, Wan CF, Wang ZY. Org. Lett. 2010; 12: 2841
    • 19e Yan YZ, Wang ZY. Chem. Commun. (Cambridge) 2011; 47: 9513
    • 19f Yan YZ, Zhang YH, Feng CT, Zha ZG, Wang ZY. Angew. Chem. Int. Ed. 2012; 51: 8077
    • 20a Witt A, Bergman J. Curr. Org. Chem. 2003; 7: 659
    • 20b Connolly DJ, Cusack D, O’Sullivan TP, Guiry PJ. Tetrahedron 2005; 61: 10153
    • 20c Liu XW, Fu H, Jiang YY, Zhao YF. Angew. Chem. Int. Ed. 2009; 48: 348
    • 20d Li JR, Chen X, Shi DX, Ma SL, Li Q, Zhang Q, Tang JH. Org. Lett. 2009; 11: 1193
    • 21a Wang SJ, Wang ZY, Zha ZG. Dalton Trans. 2009; 9363
    • 21b Wang Y, Zhu DP, Tang L, Wang SJ, Wang ZY. Angew. Chem. Int. Ed. 2011; 50: 8917
    • 22a Ward RS. Nat. Prod. Rep. 1993; 10: 1
    • 22b Ward RS. Nat. Prod. Rep. 1995; 12: 183
    • 22c Ward RS. Nat. Prod. Rep. 1997; 14: 43
    • 22d Valcic S, Montenegro G, Timmermann BN. J. Nat. Prod. 1998; 61: 771
    • 22e Cho JY, Baik KU, Yoo ES, Yoshikawa K, Park MH. J. Nat. Prod. 2000; 63: 1205
    • 22f Li SY, Fuchino H, Kawahara N, Sekita S, Satake M. J. Nat. Prod. 2002; 65: 262
  • 23 Akai S, Morita N, Iio K, Nakamura Y, Kita Y. Org. Lett. 2000; 2: 2279
    • 24a Wang JS, Matyjaszewski K. J. Am. Chem. Soc. 1995; 117: 5614
    • 24b Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
    • 24c Müller TE, Beller M. Chem. Rev. 1998; 98: 675
    • 24d Trost BM. Science (Washington, D. C.) 1991; 254: 1471
    • 25a Nicolaou KC, Baran PS, Zhong YL. J. Am. Chem. Soc. 2001; 123: 3183
    • 25b Dohi T, Takenaga N, Goto A, Fujioka H, Kita Y. J. Org. Chem. 2008; 73: 7365
    • 25c Marwah P, Marwah A, Lardy HA. Green Chem. 2004; 6: 570
    • 25d Khan AT, Parvin T, Choudhury LH, Ghosh S. Tetrahedron Lett. 2007; 48: 2271
    • 25e Sawatari N, Sakaguchi S, Ishii Y. Tetrahedron Lett. 2003; 44: 2053
    • 25f Nechab M, Einhorn C, Einhorn J. Chem. Commun. (Cambridge) 2004; 1500
    • 25g Yang G, Zhang Q, Miao H, Tong X, Xu J. Org. Lett. 2005; 7: 263
    • 26a Joule JA, Mills K. Heterocyclic Chemistry . 4th ed. Blackwell; Oxford: 2000
    • 26b Michael JP. Nat. Prod. Rep. 2005; 22: 627
    • 26c Chichibabin AE. J. Russ. Phys.-Chem. Soc. 1906; 37: 1229
    • 26d Hantzsch A. Justus Liebigs Ann. Chem. 1882; 215: 1
    • 26e Movassaghi M, Hill MD, Ahmad OK. J. Am. Chem. Soc. 2007; 129: 10096
    • 26f Kelly TR, Liu H. J. Am. Chem. Soc. 1985; 107: 4998
    • 26g Parthasarathy K, Jeganmohan M, Cheng CH. Org. Lett. 2008; 10: 325
    • 26h Wang Q, Wan CF, Gu Y, Zhang JT, Gao LF, Wang ZY. Green Chem. 2011; 13: 578
    • 27a Bi HP, Zhao L, Liang YM, Li CJ. Angew. Chem. Int. Ed. 2009; 48: 792
    • 27b Bi HP, Chen WW, Liang YM, Li CJ. Org. Lett. 2009; 11: 3246
    • 27c Myers AG, Tanaka D, Mannio MR. J. Am. Chem. Soc. 2002; 124: 11250
    • 27d Rayabarapu DK, Tunge JA. J. Am. Chem. Soc. 2005; 127: 13510
    • 27e Goossen LJ, Deng G, Levy LM. Science (Washington, D. C.) 2006; 313: 662
    • 27f Burger EC, Tunge JA. J. Am. Chem. Soc. 2006; 128: 10002
    • 28a Hamdouni NE, Companyó X, Rios R, Moyano A. Chem. Eur. J. 2010; 16: 1142
    • 28b Li Z, Jiang YY, Yeagley AA, Bour JP, Liu L, Chruma JJ, Fu Y. Chem. Eur. J. 2012; 18: 14527
    • 28c Srivastava VP, Patel R, Yadav LD. S. Adv. Synth. Catal. 2011; 353: 695
    • 29a Forsyth CJ, Ahmed F, Cink RD, Lee CS. J. Am. Chem. Soc. 1998; 120: 5597
    • 29b Jin Z. Nat. Prod. Rep. 2006; 23: 464
    • 29c Burgett AW. G, Li Q, Wei Q, Harran PG. Angew. Chem. Int. Ed. 2003; 42: 4961
    • 29d Wipf P. Chem. Rev. 1995; 95: 2115
    • 29e Riego E, Hernández D, Albericio F, Álvarez M. Synthesis 2005; 1907
    • 29f Kende AS, Kawamura K, DeVita RJ. J. Am. Chem. Soc. 1990; 112: 4070
    • 29g Vedejs E, Barda DA. Org. Lett. 2000; 2: 1033
    • 30a Japp FR, Murry TS. J. Chem. Soc. 1893; 63: 469
    • 30b Bonne D, Dekhane M, Zhu J.-P. Angew. Chem. Int. Ed. 2007; 46: 2485
    • 30c Clapham B, Spanka C, Janda KD. Org. Lett. 2001; 3: 2173
    • 30d Santos A, Kaim LE, Grimaud L, Ronsseray C. Chem. Commun. (Cambridge) 2009; 3907
    • 30e Williams DR, Fu LF. Org. Lett. 2010; 12: 808
    • 30f Tarzia G, Schiatti P, Selva D, Favara D, Ceriani S. Eur. J. Med. Chem. 1976; 11: 263
    • 30g Davies JR, Kane PD, Moody CJ. Tetrahedron 2004; 60: 3967
    • 31a Tu WY, Liu L, Floreancig PE. Angew. Chem. Int. Ed. 2008; 47: 4184
    • 31b Fan RH, Li WX, Pu DM, Zhang L. Org. Lett. 2009; 11: 1425
    • 31c Bajracharya GB, Daugulis O. Org. Lett. 2008; 10: 4625
    • 31d Zhang Y, Li C.-J. J. Am. Chem. Soc. 2006; 128: 4242
    • 32a Armstrong A, Collins JC. Angew. Chem. Int. Ed. 2010; 49: 2282 ; Angew. Chem. 2010, 122, 2332
    • 32b Thansandote P, Lautens M. Chem. Eur. J. 2009; 15: 5874
    • 32c Collet F, Dodd RH, Dauban P. Chem. Commun. (Cambridge) 2009; 5061
    • 32d Davies HM. L, Manning JR. Nature (London) 2008; 451: 417
    • 32e Dick AR, Sanford MS. Tetrahedron 2006; 62: 2439
    • 32f Davies HM. L, Long MS. Angew. Chem. Int. Ed. 2005; 44: 3518 ; Angew. Chem. 2005, 117, 3584
    • 32g Müller P, Fruit C. Chem. Rev. 2003; 103: 2905
    • 32h Collet F, Lescot C, Dauban P. Chem. Soc. Rev. 2011; 40: 1926
    • 32i Zalatan DN, Bois JD. Top. Curr. Chem. 2010; 292: 347
    • 33a Kim HJ, Kim J, Cho SH, Chang S. J. Am. Chem. Soc. 2011; 133: 16382
    • 33b Souto JA, Zian D, Muñiz K. J. Am. Chem. Soc. 2012; 134: 7242
    • 34a Halabalaki M, Aligiannis N, Papoutsi Z, Mitakou S, Moutsatsou P, Sekeris C, Skaltsounis A.-L. J. Nat. Prod. 2000; 63: 1672
    • 34b Pacher T, Seger C, Engelmeier D, Vajrodaya S, Hofer O, Greger H. J. Nat. Prod. 2002; 65: 820
    • 34c Wallez V, Durieux-Poissonnier S, Chavatte P, Boutin JA, Audinot V, Nicolas J.-P, Bennejean C, Delagrange P, Renard P, Lesieur D. J. Med. Chem. 2002; 45: 2788
    • 34d Park KK, Jeong J. Tetrahedron 2005; 61: 545
    • 34e Pan CF, Ma ZX, Yu J, Zhang ZH, Hui AL, Wang ZY. Synlett 2005; 12: 1922
    • 35a Horton DA, Bourne GT, Smythe ML. Chem. Rev. 2003; 103: 893
    • 35b Willis MC, Taylor D, Gillmore AT. Org. Lett. 2004; 6: 4755
    • 35c McKiernan GJ, Hartley RC. Org. Lett. 2003; 5: 4389
    • 35d Kraus GA, Zhang N, Verkade JG, Nagarajan M, Kisanga PB. Org. Lett. 2000; 2: 2409
    • 35e Clerici A, Porta O. J. Org. Chem. 1990; 55: 1240
    • 35f Yue D, Yao T, Larock RC. J. Org. Chem. 2005; 70: 10292
    • 35g Kraus GA, Schroeder JD. Synlett 2005; 2504