One-pot Suzuki-Miyaura cross-coupling followed by reductive monoalkylation of the resulting nitro biaryl system utilizing Pd/C as catalyst

Tetrahedron Letters

Volumn 54, Issue 35, 2013, Pages 4772-4775

  Pedersen, Lena ^a   Mady, Mohamed F ^a,b   Sydnes, Magne O ^a  

^a UNIVERSITY OF STAVANGER   (Norway)

^b NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

Catalysis; One pot; Pd C; Reductive monoalkylation; Suzuki Miyaura cross coupling

Indexed keywords

ALDEHYDE; BORONIC ACID DERIVATIVE; CARBON; GLYCERYL TRINITRATE; HYDROGEN; NITROBENZENE; PALLADIUM;

ALKYLATION; ARTICLE; CATALYST; CROSS COUPLING REACTION; SUZUKI REACTION; SYNTHESIS;

EID: 84880782349     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.06.128     Document Type: Article

References (39)

1. L.F. Tietze, and U. Beifuss Angew. Chem., Int. Ed. Engl. 32 1993 131
2. L.F. Tietze Chem. Rev. 96 1996 115
3. S.J. Broadwater, S.L. Roth, K.E. Price, and D.T. McQuade Org. Biomol. Chem. 3 2005 2899
4. M. Platon, R. Amardeil, L. Djakovitch, and J.-C. Herso Chem. Soc. Rev. 41 2012 3929
5. R.C. Wende, and P.R. Schreiner Green Chem. 14 2012 1821
6. N. Ono The Nitro Group in Organic Synthesis 2001 Wiley New York pp 3-9
7. N. Ono The Nitro Group in Organic Synthesis 2001 Wiley New York pp 170-172
8. R.N. Salvatore, C.H. Yoon, and K.W. Jung Tetrahedron 57 2001 7785
9. Z. Xiaojian, W. Zuwang, L. Li, W. Guijuan, and L. Jiaping Dyes Pigments 36 1998 365
10. J.W. Bae, Y.J. Cho, S.H. Lee, C.-O.M. Yoon, and C.M. Yoon Chem. Commun. 2000 1857
11. H. Sajiki, T. Ikawa, and K. Hirota Org. Lett. 6 2004 4977
12. H. Sajiki, T. Ikawa, and K. Hirota Org. Process Res. Dev. 9 2005 219
13. R. Nacario, S. Kotakonda, D.M.D. Fouchard, L.M.V. Tillekeratne, and R.A. Hudson Org. Lett. 7 2005 471
14. D.M.D. Fouchard, L.M.V. Tillekeratne, and R.A. Hudson Synthesis 2005 17
15. C.R. Reddy, K. Vijeender, P.B. Bhusan, P.P. Madhavi, and S. Chandrasekhar Tetrahedron Lett. 48 2007 2765
16. E. Byun, B. Hong, K.A. De Castro, M. Lim, and H. Rhee J. Org. Chem. 72 2007 9815 9817
17. C.-C. Lee, and S.-T. Liu Chem. Commun. 2011 6981
18. C. del Pozo, A. Corma, M. Iglesias, and F. Sánchez J. Catal. 291 2012 110
19. B. Sreedhar, and V.S. Rawat Synth. Commun. 42 2012 2490
20. Y. Xie, S. Liu, Y. Liu, Y. Wen, and G.-J. Deng Org. Lett. 14 2012 1692
21. T. Ikawa, Y. Fujita, T. Mizusaki, S. Betsuin, H. Takamatsu, T. Maegawa, Y. Monguchi, and H. Sajiki Org. Biomol. Chem. 10 2012 293
22. H. Li, Z. Dong, P. Wang, F. Zhang, and J. Ma React. Kinet. Mech. Catal. 108 2013 107
23. M.O. Sydnes, and M. Isobe Tetrahedron Lett. 49 2008 1199
24. M.O. Sydnes, M. Kuse, and M. Isobe Tetrahedron 64 2009 6406
25. Y. Kitamura, S. Sako, T. Udzu, A. Tsutsui, T. Maegawa, Y. Monguchi, and H. Sajiki Chem. Commun. 2007 5069
26. T. Maegawa, Y. Kitamura, S. Sako, T. Udzu, A. Sakurai, A. Tanaka, Y. Kobayashi, K. Endo, U. Bora, T. Kurita, A. Kozaki, Y. Monguchi, and H. Sajiki Chem. Eur. J. 13 2007 5937
27. Y. Kitamura, A. Sakurai, T. Udzu, T. Maegawa, Y. Monguchi, and H. Sajiki Tetrahedron 63 2007 10596
28. Y. Kitamura, S. Sako, A. Tsutsui, Y. Monguchi, T. Maegawa, Y. Kitade, and H. Sajiki Adv. Synth. Catal. 352 2010 718
29. Y. Monguchi, Y. Fujita, S. Hashimoto, M. Ina, T. Takahashi, R. Ito, K. Nozaki, T. Maegawa, and H. Sajiki Tetrahedron 67 2011 8628
30. For recent reviews discussing the use of Pd/C in cross-coupling reactions, see: M.O. Sydnes Curr. Org. Synth. 8 2011 881
31. M. Mora, C. Jimenez-Sanchidrian, and J.R. Ruiz Curr. Org. Chem. 16 2012 1128
32. Sajiki et al. have also started utilizing palladium supported on a synthetic adsorbent for ligand-free cross-coupling reactions, see: Y. Monguchi, Y. Fujita, K. Endo, S. Takao, M. Yoshimura, Y. Takagi, T. Maegawa, and H. Sajiki Chem. Eur. J. 15 2009 834
33. Y. Monguchi, K. Sakai, K. Endo, K. Fujita, M. Niimura, M. Yoshimura, T. Mizusaki, Y. Sawama, and H. Sajiki ChemCatChem 4 2012 546
34. A. Simion, C. Simion, T. Kanda, S. Nagashima, Y. Mitoma, T. Yamada, K. Mimura, and M. Tashiro J. Chem. Soc., Perkin Trans. 1 2001 2071
35. C. Cody-Alcantar, A.K. Yatsimirsky, and J.-M. Lehn J. Phys. Org. Chem. 18 2005 979
36. V. Saggiomo, and U. Lüning Eur. J. Org. Chem. 25 2008 4329
37. V. Saggiomo, and U. Lüning Tetrahedron Lett. 50 2009 4663
38. A. Corma, S. Iborra, and A. Velty Chem. Rev. 107 2007 2411
39. S. Sitthisa, and D.E. Resasco Catal. Lett. 141 2011 784