Palladium complexes containing multidentate phenoxy-pyridyl-amidate ligands: Highly efficient catalyst for Heck coupling of deactivated aryl halides

Journal of Organometallic Chemistry

Volumn 723, Issue , 2013, Pages 129-136

  Kantam, M Lakshmi ^a   Annapurna, Manne ^a   Likhar, Pravin R ^a   Srinivas, P ^a   Mirzadeh, Nedaossadat ^b   Bhargava, Suresh K ^a,b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b RMIT UNIVERSITY   (Australia)

Author keywords

Heck reaction; High turnover; N ligand; Palladium; Phosphine free

Indexed keywords

ARYL BROMIDES; ARYL CHLORIDE; ARYL HALIDES; EFFICIENT CATALYSTS; HECK COUPLING; HECK REACTIONS; HIGH TURNOVER; MULTIDENTATE; N LIGANDS; PALLADIUM COMPLEXES; PHOSPHINE-FREE; TURNOVER NUMBER;

AMINO ACIDS; CATALYSTS; CHEMICAL REACTIONS; CHLORINE COMPOUNDS; LIGANDS; METAL HALIDES; PALLADIUM; PHOSPHORUS COMPOUNDS;

PALLADIUM COMPOUNDS;

EID: 84868537012     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2012.08.037     Document Type: Article

References (46)

1. I.P. Beletskaya, and A.V. Cheprakov Chem. Rev. 100 2000 3009 3066
2. N.T.S. Phan, M. Van Der Sluys, and C.W. Jones Adv. Synth. Catal. 348 2006 609 679
3. F. Alonso, I.P. Beletskaya, and M. Yus Tetrahedron 61 2005 11771 11835
4. J.T. Link, and L.E. Overman F. Diederich, P.J. Stang, Metal-Catalyzed Cross-Coupling Reactions 1998 Wiley-VCH Weinheim (Chapter 6)
5. J.L. Hedrick, and J.W. Labadie Step-Growth Polymers for High-Performance Materials ACS Symposium Series vol. 624 1996 American Chemical Society Washington, DC (Chapters 1, 2, and 4)
6. A. Häberli, and C.J. Leumann Org. Lett. 3 2001 489 492
7. M. Feuerstein, H. Doucet, and M. Santelli J. Org. Chem. 66 2001 5923 5925
8. C.M. So, C.P. Lau, A.S.C. Chan, and F.Y. Kwong J. Org. Chem. 73 2008 7731 7734
9. L.R. Moore, and K.H. Shaughnessy Org. Lett. 6 2004 225 228
10. D. Bourissou, O. Guerret, F.P. Gabbaï, and G. Bertrand Chem. Rev. 100 2000 39 91
11. X. Zhang, Z. Xi, A. Liu, and W. Chen Organometallics 27 2008 4401 4406
12. D. Meyer, M.A. Taige, A. Zeller, K. Hohlfeld, S. Ahrens, and T. Strassner Organometallics 28 2009 2142 2149
13. W.A. Herrmann, K. Öfele, S.K. Schneider, E. Herdtweck, and S.D. Hoffmann Angew. Chem. Int. Ed. 45 2006 3859 3862
14. D.F. Wass, M.F. Haddow, T.W. Hey, A. Guy Orpen, C.A. Russell, R.L. Wingad, and M. Green Chem. Commun. 2007 2704 2706
15. Q. Yao, M. Zabawa, J. Woo, and C. Zheng J. Am. Chem. Soc. 129 2007 3088 3089
16. R.A. Gossage, H.A. Jenkins, and P.N. Yadav Tetrahedron Lett. 45 2004 7689 7691
17. K.-M. Wu, C.-A. Huang, K.-F. Peng, and C.-T. Chen Tetrahedron 61 2005 9679 9687
18. T. Kawano, T. Shinomaru, and I. Ueda Org. Lett. 4 2002 2545 2547
19. C. Nájera, J. Gil-Moltó, S. Karlström, and L.R. Falvello Org. Lett. 5 2003 1451 1454
20. B. Tao, and D.W. Boykin J. Org. Chem. 69 2004 4330 4335
21. J.C. Xiao, B. Twamley, and J.M. Shreeve Org. Lett. 6 2004 3845 3847
22. S.B. Park, and H. Alper Org. Lett. 5 2003 3209 3212
23. V. Montoya, J. Pons, V. Branchadell, J. Garcia-Antón, X. Solans, M. Font-Bardía, and J. Ros J. Organomet. 27 2008 1084 1091
24. F. Li, and T.S. Hor Adv. Synth. Catal. 350 2008 2391 2400
25. P.J. Steel Molecules 9 2004 440 448
26. M. Guerrero, J. Pons, and J. Ross J. Organomet. Chem. 695 2010 1957 1960
27. L.L. de Olivera, R.R. Campedelli, M.C.A. Kuhn, J.-F. Carpentier, and O.L. Casagrande Jr. J. Mol. Catal. A Chem. 288 2008 58 62
28. X. Cui, Y. Zhou, N. Wang, L. Liu, and Q.-X. Guo Tetrahedron Lett. 48 2007 163 167
29. D. Yang, Y.-C. Chen, and N.-Y. Zhu Org. Lett. 6 2004 1577 1580
30. W. Chen, R. Li, B. Han, B.J. Li, Y.-C. Chen, Y. Wu, L.S. Ding, and D. Yang Eur. J. Org. Chem. 2006 1177 1184
31. M.J. Dai, B. Liang, C.H. Wang, Z.J. You, J. Xiang, G.B. Dong, J.H. Chen, and Z. Yang Adv. Synth. Catal. 346 2004 1669 1673
32. A.K. Gupta, C.H. Song, and C.H. Oh Tetrahedron Lett. 45 2004 4113 4116
33. M.T. Reetz, E. Westermann, R. Lohmer, and G. Lohmer Tetrahedron Lett. 39 1998 8449 8452
34. P. Srinivas, P.R. Likhar, H. Maheswaran, B. Sridhar, K. Ravikumar, and M.L. Kantam Chem. Eur. J. 15 2009 1578 1581
35. P. Srinivas, K. Srinivas, P.R. Likhar, B. Sridhar, K.V. Mohan, S. Bhargava, and M.L. Kantam J. Organomet. Chem. 696 2011 795 801
36. M.L. Kantam, P. Srinivas, J. Yadav, P.R. Likhar, and S. Bhargava J. Org. Chem. 74 2009 4882 4885
37. Y.-Q. Gong, Y.-F. Cheng, J.-M. Gu, and X.-R. Hu Polyhedron 16 1997 3743 3746
38. S. Iwatsuki, T. Suzuki, T. Yajima, T. Shiraiwa, O. Yamauchi, and Y. Shimazaki Inorg. Chim. Acta 377 2011 111 119
39. Y.-C. Lai, H.-Y. Chen, W.-C. Hung, C.-C. Lin, and F.-E. Hong Tetrahedron 61 2005 9484 9489
40. A.H.M. de Vries, J.M.C.A. Mulders, J.H.M. Mommers, H.J.W. Henderickx, and J.G. de Vries Org. Lett. 5 2003 3285 3288
41. Q. Yao, E.P. Kinney, and Z. Yang J. Org. Chem. 68 2003 7528 7531
42. V. Farina Adv. Synth. Catal. 346 2004 1553 1582
43. SMART Ver. 5.625 Software for the CCD Detector System 2001 Bruker AXS Inc. Madison, WI
44. SAINTPLUS Ver. 6.22 Software for the CCD Detector System 2001 Bruker AXS Inc. Madison, WI
45. SADABS program for absorption correction using SMART CCD data based on the method of Blessing R.H. Blessing Acta Crystallogr. Sect. A 51 1995 33 38
46. G.M. Sheldrick SHELXTL, Ver. 6.10 1994 University of Göttingen Germany