Citation: Peng Lifen, Hu Zhifang, Tang Zilong, Jiao Yinchun, Xu Xinhua. Recent progress in transition metal catalyzed cross coupling of nitroarenes[J]. Chinese Chemical Letters, ;2019, 30(8): 1481-1487. doi: 10.1016/j.cclet.2019.04.008 shu

Recent progress in transition metal catalyzed cross coupling of nitroarenes

Peng Lifen ^a,*, ,
Hu Zhifang ^a ,
Tang Zilong ^a,*, ,
Jiao Yinchun ^a ,
Xu Xinhua ^b

a.
Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China
b.
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China

1060137@hnust.edu.cn

zltang@hnust.edu.cn

Received Date: 27 January 2019
Revised Date: 22 March 2019
Accepted Date: 1 April 2019
Available Online: 3 August 2019

Figures(14)

In this review, the recent development in transition metal catalyzed cross coupling of nitroarenes was highlighted. Firstly, development of transition metal catalyzed cross coupling was simply introduced. After presenting the advantages of nitroarenes, transition metal catalyzed cross coupling using nitroarenes as electrophilic coupling partners was classified and introduced in detail. Based on different chemical bonds such as C–O, C–S, C–C and C–N bonds constructed, different kinds cross coupling of nitroarenes would be highlighted and the plausible reaction mechanism would be presented if available.
- Transition metal,
- Catalysis,
- Nitroarenes,
- Cross coupling,
- Chemical bonds
1. [1]
  (a) N. Miyaura, A. Suzuki, Chem. Rev. 95 (1995) 2457-2483;
  (b) B. Zhang, R. Breslow, J. Am. Chem. Soc. 119 (1997) 1676-1681;
  (c) Ei. Negishi, Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, 1998;
  (d) A. Minato, K. Suzuki, K. Tamao, M. Kumada, J. Chem. Soc. Chem. Commun. 8 (1984) 511-513;
  (e) A.F. Littke, G.C. Fu, Angew. Chem. Int. Ed. 41 (2002) 4176-4211;
  (f) A.R. Chinchilla, C. Nájera, Chem. Rev. 107 (2007) 874-922;
  (g) L.F. Peng, S.W. Zhang, B.H. Wang, et al., Chin. J. Org. Chem. 38 (2018) 519-525.
2. [2]
  (a) X. Li, J.W. Han, H.N.C. Wong, Asian J. Org. Chem. 5 (2016) 74-81;
  (b) K.C. Nicolaou, P.G. Bulger, D. Sarlah, Angew. Chem. Int. Ed. 44 (2005) 4442-4489;
  (c) L.F. Peng, B.H. Wang, M. Wang, et al., J. Chem. Res. 42 (2018) 235-238;
  (d) L.F. Peng, J.Y. Lei, L. Wu, et al., J. Chem. Res. 42 (2018) 271-273;
  (e) L.F. Peng, C. Peng, M. Wang, et al., Chin. J. Org. Chem. 38 (2018) 3048-3055;
  (f) R. Jana, T.P. Pathak, M.S. Sigman, Chem. Rev. 111 (2011) 1417-1492.
3. [3]
  (a) J. Magano, J.R. Dunetz, Chem. Rev. 111 (2011) 2177-2250;
  (b) T.E. Barder, S.D. Walker, J.R. Martinelli, S.L. Buchwald, J. Am. Chem. Soc. 127 (2005) 4685-4696;
  (c) S. Abbas, L. Ferris, A.K. Norton, Org. Process Res. Dev. 12 (2008) 202-212;
  (d) S. Yu, A. Haight, B. Kotecki, et al., J. Org. Chem. 74 (2009) 9539-9542;
  (e) J.Q. Wan, Y. Xia, Y. Liu, et al., J. Med. Chem. 52 (2009) 1144-1155.
4. [4]
  (a) M.S. Karatholuvhu, A. Sinclair, A.F. Newton, et al., J. Am. Chem. Soc. 128 (2006) 12656-12657;
  (b) Q. Su, L.A. Dakin, J.S. Panek, J. Org. Chem. 72 (2007) 2-24;
  (c) V.V. Vintonyak, B. Kunze, F. Sasse, M.E. Maier, Chem.-Eur. J.14 (2008) 11132-11140;
  (d) G. Dyker, D. Hildebrandt, J. Org. Chem. 70 (2005) 6093-6096.
5. [5]
  (a) C.K. Hau, S.S.Y. Chui, W. Lu, Chem. Sci. 2 (2011) 1068-1075;
  (b) C.L. Deng, X.D. Xiong, D.T.W. Chik, Chem.-Asian J. 10 (2015) 2342-234;
  (c) Y. Yamaguchi, T. Ochi, T. Wakamiya, Y. Matsubara, Z. Yoshida, Org. Lett. 8 (2006) 717-720;
  (d) J.N. Wilson, M. Josowicz, Y. Wang, U.H.F. Bunz, Chem. Commun. (2003) 2982-2983;
  (e) H. Sugiura, Y. Nigorikawa, Y. Saiki, K. Nakamura, M. Yamaguchi, J. Am. Chem. Soc. 126 (2004) 14858-14864;
  (f) T.L. Wu, H.H. Chou, P.Y. Huang, C.H. Cheng, R.S. Liu, J. Org. Chem. 79 (2014) 267-274;
  (g) J. Kim, A.R. Han, J. Hong, et al., Chem. Mater. 26 (2014) 4933-4942;
  (h) P. Deria, C.D. Von Bargen, J.H. Olivier, et al., J. Am. Chem. Soc. 135 (2013) 16220-16234;
  (i) Z.Y. Yao, M. Zhang, H. Wu, et al., J. Am. Chem. Soc. 137 (2015) 3799-3802.
6. [6]
  (a) A.F. Littke, G.C. Fu, Angew. Chem. Int. Ed. 41 (2002) 4176-4211;
  (b) P. Fitton, E.A. Rick, J. Organomet. Chem. 28 (1971) 287-291;
  (c) R. Stürmer, Angew. Chem. 111 (1999) 3509-3510.
7. [7]
  (a) V.V. Grushin, H. Alper, Chem. Rev. 94 (1994) 1047-1062;
  (b) R. Stürmer, Angew. Chem. Int. Ed. 38 (1999) 3307-3308;
  (c) H.U. Blaser, E. Schmidt, Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 2004;
  (d) S.L. Buchwald, C. Mauger, G. Mignani, U. Scholz, Adv. Synth. Catal. 348 (2006) 23-39;
  (e) B. Schlummer, U. Scholz, Adv. Synth. Catal. 346 (2004) 1599-1626;
  (f) H.U. Blaser, A. Indolese, F. Naud, U. Nettekoven, A. Schnyder, Adv. Synth. Catal. 346 (2004) 1583-1598;
  (g) C. Torborg, M. Beller, Adv. Synth. Catal. 351 (2009) 3027-3043;
  (h) F. Naso, F. Babudri, G.M. Farinola, Pure Appl. Chem. 71 (1999) 1485-1492;
  (i) R.N. Yi, Z.J. Wang, Z.W. Liang, et al., Appl. Organomet. Chem. 33 (2019) e4917-e4923.
8. [8]
  (a) C.C.C. Johansson Seechurn, M.O. Kitching, T.J. Colacot, V. Snieckus, Angew. Chem. Int. Ed. 51 (2012) 5062-5085;
  (b) C.C.C. Johansson Seechurn, M.O. Kitching, T.J. Colacot, V. Snieckus, Angew. Chem. 124 (2012) 5150-5174.
9. [9]
  (a) Z.H. Jia, Liu Q, X.S. Peng, H.N.C. Wong, Nat. Commun. 7 (2016) 10614-10620;
  (b) C. Han, S.L. Buchwald, J. Am. Chem. Soc. 131 (2009) 7532-7533;
  (c) B.D. Sherry, A. Fürstner, Acc. Chem. Res. 41 (2008) 1500-1511;
  (d) S.M. Neumann, J.K. Kochi, J. Org. Chem. 40 (1975) 599-606;
  (e) A. Fürstner, A. Leitner, Angew. Chem. Int. Ed. 41 (2002) 609-612;
  (f) B.J. Li, L. Xu, Z.H. Wu, et al., J. Am. Chem. Soc. 131 (2009) 14656-14657;
  (g) C.S. Yeung, V.M. Dong, J. Am. Chem. Soc. 130 (2008) 7826-7827;
  (h) J. Zhou, G.C. Fu, J. Am. Chem. Soc. 125 (2003) 14726-14727;
  (i) K. Tamao, Y. Kiso, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 94 (1972) 9268-9269.
10. [10]
  (a) D.W. Old, J.P. Wolfe, S.L. Buchwald, J. Am. Chem. Soc.120 (1998) 9722-9723;
  (b) J.P. Wolfe, R.A. Singer, B.H. Yang, S.L. Buchwald, J. Am. Chem. Soc.121 (1999) 9550-9561;
  (c) M. Schomaker, T.J. Delia, J. Org. Chem. 66 (2001) 7125-7128;
  (d) A.J. Cocuzza, D.R. Chidester, S. Culp, L. Fitzgerald, P. Gilligan, Bioorg. Med. Chem. Lett. 9 (1999) 1063-1066;
  (e) J.P. Wolfe, S.L. Buchwald, Angew. Chem. 111 (1999) 2570-2573.
11. [11]
  (a) J.M. Lovell, J.A. Joule, Synth. Commun. 27 (1997) 1209-1215;
  (b) A. Suzuki, J. Organomet. Chem. 576 (1999) 147-168;
  (c) G.B. Smith, G.C. Dezeny, D.L. Hughes, A.O. King, T.R. Verhoeven, J. Org. Chem. 59 (1994) 8151-8156.
12. [12]
  J. Zhang, J. Chen, M. Liu, X. Zheng, J. Ding, H. Wu, Green Chem. 14 (2012) 912-916. doi: 10.1039/c2gc16539b
13. [13]
  (a) K. Itami, M. Mineno, N. Muraoka, J.I. Yoshida, J. Am. Chem. Soc. 126 (2004) 11778-11779;
  (b) L.W. Qian, M. Sun, J. Dong, Q. Xu, Y. Zhou, S.F. Yin, J. Org. Chem. 82 (2017) 6764-6769;
  (c) K. Itami, D. Yamazaki, J.I. Yoshida, J. Am. Chem. Soc.126 (2004) 5396-15397;
  (d) S.R. Dubbaka, P. Vogel, Angew. Chem. Int. Ed. 44 (2005) 7674-7684;
  (e) S.R. Dubbaka, P. Vogel, Tetrahedron Lett. 47 (2006) 3345-3348;
  (f) P. Leowanawat, N. Zhang, A.M. Resmerita, B.M. Rosen, V. Percec, J. Org. Chem. 76 (2011) 9946-9955.
14. [14]
  (a) D. Gärtner, A.L. Stein, S. Grupe, J. Arp, A.J. Wangelin, Angew. Chem. Int. Ed. 54 (2015) 10545-10549;
  (b) M.R. Harris, L.E. Hanna, M.A. Greene, C.E. Moore, E.R. Jarvo, J. Am. Chem. Soc. 135 (2013) 3303-3306;
  (c) K.W. Quasdorf, X. Tian, N.K. Garg, J. Am. Chem. Soc. 130 (2008) 14422-14423.
15. [15]
  (a) G.G. Meng, S.C. Shi, M. Szostak, ACS Catal. 6 (2016) 7335-7339;
  (b) K.R. Buszek, N. Brown, Org. Lett. 9 (2007) 707-710;
  (c) M. Barbero, S. Dughera, Tetrahedron 74 (2018) 5758-5769;
  (d) Y. Bourne-Branchu, C. Gosmini, G. Danoun, Chem.-Eur. J. 25 (2019) 2663-2674.
16. [16]
  (a) H. Li, J. Liu, C.L. Sun, B.J. Li, Z.J. Shi, Org. Lett. 13 (2011) 276-279;
  (b) S. Tang, L. Zeng, A.W. Lei, J. Am. Chem. Soc. 140 (2018) 13128-13135;
  (c) Q. Zhang, Y. Liu, T. Wang, et al., J. Am. Chem. Soc. 140 (2018) 5579-5587;
  (d) M. Shang, H.L. Wang, S.Z. Sun, H.X. Dai, J.Q. Yu, J. Am. Chem. Soc. 136 (2014) 11590-11593.
17. [17]
  G. Booth, Nitro Compounds, Aromatic; Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, New York, 2012.
18. [18]
  Y. Yang, Angew. Chem. Int. Ed. 56 (2017) 15802-15804. doi: 10.1002/anie.201708940
19. [19]
  X.W. Zheng, J.C. Ding, J.X. Chen, et al., Org. Lett. 13 (2011) 1726-1729. doi: 10.1021/ol200251x
20. [20]
  J.L. Zhang, J.X. Chen, M.C. Liu, et al., Green Chem. 14 (2012) 912-916. doi: 10.1039/c2gc16539b
21. [21]
  D.P. Peng, A.J. Yu, H.L. Wang, Y.J. Wu, J.B. Chang, Tetrahedron 69 (2013) 6884-6889. doi: 10.1016/j.tet.2013.05.112
22. [22]
  H.L. Wang, A.J. Yu, A.J. Cao, J.B. Chang, Y.J. Wu, Appl. Organomet. Chem. 27 (2013) 611-614.
23. [23]
  T. Begum, M. Mondal, M.P. Borpuzari, et al., Eur. J. Org. Chem. (2017) 3244-3248.
24. [24]
  S.S. Bahekar, A.P. Sarkate, V.M. Wadhai, P.S. Wakte, D.B. Shinde, Catal. Commun. 41 (2013) 123-125. doi: 10.1016/j.catcom.2013.07.019
25. [25]
  H. Tian, A.J. Cao, L.J. Qiao, et al., Tetrahedron 70 (2014) 9107-9112. doi: 10.1016/j.tet.2014.09.087
26. [26]
  A. Rostami, A. Rostami, A. Ghaderi, J. Org. Chem. 80 (2015) 8694-8704. doi: 10.1021/acs.joc.5b01248
27. [27]
  B.P. Fors, S.L. Buchwald, J. Am. Chem. Soc. 131 (2009) 12898-12899. doi: 10.1021/ja905768k
28. [28]
  M.R. Yadav, M. Nagaoka, M. Kashihara, et al., J. Am. Chem. Soc.139 (2017) 9423-9426. doi: 10.1021/jacs.7b03159
29. [29]
  F. Inoue, M. Kashihara, M.R. Yadav, Y. Nakao, Angew. Chem. Int. Ed. 56 (2017) 13307-13309. doi: 10.1002/anie.201706982
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