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

Sindre Å. Lunde; Magne O. Sydnes

doi:10.1055/s-0033-1339860

Synlett, Table of Contents

Synlett 2013; 24(18): 2340-2344
DOI: 10.1055/s-0033-1339860

synpacts

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

Authors

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

Abstract

All articles of this category

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.

Key words

one pot - Suzuki–Miyaura cross-coupling - reductive monoalkylation - biaryl - secondary amine

Full Text

References

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