Synlett 2013; 24(18): 2340-2344
DOI: 10.1055/s-0033-1339860
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© Georg Thieme Verlag Stuttgart · New York

One-Pot Procedures for the Formation of Secondary Aryl Amines from Nitro Aryls

Sindre Å. Lunde
Department of Mathematics and Natural Science, Faculty of Science and Technology, University of Stavanger, 4036 Stavanger, Norway   Fax: +4751831750   Email: magne.o.sydnes@uis.no
,
Magne O. Sydnes*
Department of Mathematics and Natural Science, Faculty of Science and Technology, University of Stavanger, 4036 Stavanger, Norway   Fax: +4751831750   Email: magne.o.sydnes@uis.no
› Author Affiliations
Further Information

Publication History

Received: 24 July 2013

Accepted after revision: 03 September 2013

Publication Date:
30 September 2013 (online)

Abstract

Strategies for the one-pot formation of secondary aryl amines from the corresponding nitro aryls by utilizing reductive amination procedures are discussed. The extension of this chemistry where a Suzuki–Miyaura cross-coupling is conducted between a boronic acid and bromonitrobenzene prior to the reductive amination in one-pot is also presented.

 
  • References

  • 1 Salvatore RN, Yoon CH, Jung KW. Tetrahedron 2001; 57: 7785
  • 2 Czarnik AW. Acc. Chem. Res. 1996; 29: 112
  • 3 Perkin WH. J. Chem. Soc., Trans. 1879; 35: 717
  • 4 Dong Y, Nakagawa-Goto K, Lai C.-Y, Morris-Natschke SL, Bastow KF, Kim Y, Lee EY.-H. P, Lee K.-H. J. Nat. Prod. 2012; 75: 370
  • 5 Ono N In The Nitro Group in Organic Synthesis . Wiley; New York: 2001: 170
  • 6 Xiaojian Z, Zuwang W, Li L, Guijuan W, Jiaping L. Dyes Pigm. 1998; 36: 365
  • 7 Lee C.-C, Liu S.-T. Chem. Commun. 2011; 47: 6981
    • 8a Bae JW, Cho YJ, Lee SH, Yoon C.-OM, Yoon CM. Chem. Commun. 2000; 1857
    • 8b The chemistry described in ref. 8a was later expanded upon by Yoon and co-workers in order to prepare tertiary aromatic amines incorporating two different alkyl groups, see: Jung YJ, Bae JW, Park ES, Chang YM, Yoon CM. Tetrahedron 2003; 59: 10331
  • 9 Byun E, De Castro KA, Lim M, Rhee H. J. Org. Chem. 2007; 72: 9815
  • 10 Dell’Anna MM, Mastrorilli P, Rizzuti A, Leonelli C. Appl. Catal., A 2011; 401: 134
  • 11 del Pozo C, Corma A, Iglesias M, Sánchez F. J. Catal. 2012; 291: 110
  • 12 Li H, Dong Z, Wang P, Zhang F, Ma J. React. Kinet., Mech. Catal. 2013; 108: 107
  • 13 Li L, Niu Z, Cai S, Zhi Y, Li H, Rong H, Liu L, Liu L, He W, Li Y. Chem. Commun. 2013; 49: 6843
  • 14 Pintado-Sierra M, Rasero-Almansa AM, Corma A, Iglesias M. J. Catal. 2013; 299: 137
  • 15 Sreedhar B, Rawat VS. Synth. Commun. 2012; 42: 2490
  • 16 Wahba AE, Hamann MT. J. Org. Chem. 2012; 77: 4578
  • 17 Xie Y, Liu S, Liu Y, Wen Y, Deng G.-J. Org. Lett. 2012; 14: 1692
    • 18a Sajiki H, Ikawa T, Hirota K. Org. Lett. 2004; 6: 4977
    • 18b Sajiki H, Ikawa T, Hirota K. Org. Process Res. Dev. 2005; 9: 219
    • 19a Nacario R, Kotakonda S, Fouchard DM. D, Tillekeratne LM. V, Hudson RA. Org. Lett. 2005; 7: 471
    • 19b Fouchard DM. D, Tillekeratne LM. V, Hudson RA. Synthesis 2005; 17
  • 20 Reddy CR, Vijeender K, Bhusan PB, Madhavi PP, Chandrasekhar S. Tetrahedron Lett. 2007; 48: 2765
  • 21 Ikawa T, Fujita Y, Mizusaki T, Betsuin S, Takamatsu H, Maegawa T, Monguchi Y, Sajiki H. Org. Biomol. Chem. 2012; 10: 293
  • 22 Chandrasekhar S, Narsihmulu C, Jagadeshwar V. Synlett 2002; 771
  • 23 Sydnes MO, Isobe M. Tetrahedron Lett. 2008; 49: 1199
  • 24 Sydnes MO, Doi I, Ohishi A, Kuse M, Isobe M. Chem. Asian. J. 2008; 3: 102
  • 25 Esaki H, Ohtaki R, Maegawa T, Monguchi Y, Sajiki H. J. Org. Chem. 2007; 72: 2143
  • 26 Sydnes MO, Kuse M, Isobe M. Tetrahedron 2008; 64: 6406
  • 27 Greene TW, Wuts PG. M. Protective Groups in Organic Synthesis . Wiley; New York: 1999. 3rd ed., 579-580
  • 28 Sajiki H, Hirota K. Tetrahedron 1998; 54: 13981
    • 29a Kitamura Y, Sako S, Udzu T, Maegawa T, Monguchi Y, Sajiki H. Chem. Commun. 2007; 5069
    • 29b Maegawa T, Kitamura Y, Sako S, Udzu T, Sakurai A, Tanaka A, Kobayashi Y, Endo K, Bora U, Kurita T, Kozaki A, Monguchi Y, Sajiki H. Chem. Eur. J. 2007; 13: 5937
    • 29c Kitamura Y, Sakurai A, Udzu T, Maegawa T, Monguchi Y, Sajiki H. Tetrahedron 2007; 63: 10596
    • 29d Kitamura Y, Sako S, Tsutsui A, Monguchi Y, Maegawa T, Kitade Y, Sajiki H. Adv. Synth. Catal. 2010; 352: 718
    • 29e Monguchi Y, Fujita Y, Hashimoto S, Ina M, Takahashi T, Ito R, Nozaki K, Maegawa T, Sajiki H. Tetrahedron 2011; 67: 8628

      For reviews discussing heterogeneous palladium-catalyzed Suzuki–Miyaura cross-coupling reactions, see:
    • 30a Lamblin M, Nassar-Hardy L, Hierso J.-C, Fouquet E, Felpin F.-X. Adv. Synth. Catal. 2010; 352: 33
    • 30b Sydnes MO. Curr. Org. Synth. 2011; 8: 881
    • 30c Mora M, Jiménez-Sanchidrián C, Ruiz JR. Curr. Org. Chem. 2012; 16: 1128
  • 31 Pedersen L, Mady MF, Sydnes MO. Tetrahedron Lett. 2013; 54: 4772
  • 32 Figueras F, Coq B. J. Mol. Catal. A: Chem. 2001; 173: 223