Insights into the role of new palladium pincer complexes as robust and recyclable precatalysts for suzuki-miyaura couplings in neat water

Advanced Synthesis and Catalysis

Volumn 351, Issue 13, 2009, Pages 2124-2132

  Inés, Blanca ^a   Sanmartin, Raul ^a   Moure, María Jesús ^a   Domínguez, Esther ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Cross coupling; Palladium nanoparticles; Palladium pincer complexes; Precatalysts; suzuki miyaura coupling

Indexed keywords

EID: 70349427135     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900345     Document Type: Article

References (53)

1. C. J. Moulton, B. L. Shaw, J. Chem. Soc. Dalton Trans. 1976, 1020-1024.
2. The Chemistry of Pincer Compounds, 1st edn., (Eds: D. Morales-Morales, M. G. Jensen), Elsevier, Amsterdam, 2007.
3. a) K. Öfele, J. Organomet. Chem. 1968, 12, 42-43;
4. b) H. W. Wanzlick, H. J. Schönherr, Angew. Chem. 1968, 80, 154-154;
5. Angew. Chem. Int. Ed. Engl. 1968, 7, 141-142.
6. a) A. J. Arduengo, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1991, 113, 361-363;
7. b) A. A. Danopoulos, S. Winston, W. B. Motherwell, Chem. Commun. 2002, 1376-1377;
8. c) J. Y. Zeng, M. H. Hsieh, H. M. Lee, J. Organomet. Chem. 2005, 690, 5662-5671.
9. a) I. P. Beletskaya, A. N. Kashin, A. E. Litvinov, V. S. Tyurin, P. M. Valetsky, G. van Koten, Organometallics 2006, 25, 154-158;
10. b) T. Nishimura, S. Uemura, Synlett 2004, 201-216.
11. For a recent review, see: A. Chanda, V. V. Fokin, Chem. Rev. 2009, 109, 725-748.
12. a) B. Inés, R. SanMartin, F. Churruca, E. Domínguez, M. K. Urtiaga, M. I. Arriortua, Organometallics 2008, 27, 2833-2839;
13. b) B. Inés, I. Moreno, R. SanMartin, E. Domínguez, J. Org. Chem. 2008, 73, 8448-8451.
14. F. Churruca, R. SanMartin, B. Inés, I. Tellitu, E. Domínguez, Adv. Synth. Catal. 2006, 348, 1836-1840.
15. For a review see, for example: a) J. A. Widegren, R. G. Finke, J. Mol. Catal. A 2003, 198, 317-341;
16. b) N. T. S. Phan, M. Van Der Sluys, C. W. Jones, Adv. Synth. Catal. 2006, 348, 609-679.
17. R.-A. Fallahpour, Synthesis 2000, 1138-1142.
18. J. A. Loch, M. Albrecht, E. Peris, J. Mata, J. W. Faller, R. H. Crabtree, Organometallics 2002, 21, 700-706.
19. a) D. Pugh, A A. Danopoulos, Coord. Chem. Rev. 2007, 251, 610-641;
20. b) E. Peris, R. H. Crabtree, Coord. Chem. Rev. 2004, 248, 2239-2246;
21. c) R. H. Crabtree, Pure Appl. Chem. 2003, 75, 435-443;
22. d) F. E. Hahn, M. C. Jahnke, Angew. Chem. 2008, 120, 3166-3216;
23. Angew. Chem. Int. Ed. 2008, 47, 3122-3172. For the synthesis of pincer complexes bearing benzimidazolin2-ylidene moieties and their application to C-C bond forming reactions, see
24. e) F. E. Hahn, M. C. Jahnke, V. Gomez-Benitez, D. Morales-Morales, T. Pape, Organometallics 2005, 24, 6458-6463;
25. f) F. E. Hahn, M. C. Jahnke, T. Pape, Organometallics 2007, 26, 150-154.
26. a) C. Nájera, J. Gil-Moltó, S. Karlström, Adv. Synth. Catal. 2004, 346, 1789-1811;
27. b) L. Botella, C. Nájera, Angew. Chem. 2002, 114, 187-189;
28. Angew. Chem. Int. Ed. 2002, 41, 179-181;
29. c) C. K. Z. Andrade, L. M. Alves, Curr. Org. Chem. 2005, 9, 195-218.
30. A. Flaherty, A. Trunkfield, W. Barton, Org. Lett. 2005, 7, 4975-4978.
31. M. McLaughilin, Org. Lett. 2005, 7, 4875-4878.
32. R. Kuwano, M. Yokogi, Org. Lett. 2005, 7, 945-947.
33. K. Itami, M. Mineno, T. Kamei, J.-I. Yoshida, Org. Lett. 2002, 4, 3635-3638.
34. W. Dohle, D. M. Lindsay, O. Knochel, Org. Lett. 2001, 3, 2871-2873.
35. G. A. Molander, M. D. Elia, J. Org. Chem. 2006, 71, 9198-9203.
36. a) C.-P. Chang, Y. L. Huang, F.-E. Hong, Tetrahedron 2005, 61, 3835-3839;
37. b) B. P. Bandgar, S. V. Bettigeri, J. Phopase, Tetrahedron Lett. 2004, 45, 6959-6962;
38. c) S. Langle, M. Abarbi, A. Duchene, Tetrahedron Lett. 2003 44, 9255-9258.
39. a) M. R. Eberhard, Org. Lett. 2004, 6, 2125-2128;
40. b) D. E. Bergbreiter, P. L. Osburn, J. D. Frels, Adv. Synth. Catal. 2005, 347, 172-184;
41. c) L. Djakovitch, K. Köhler, J. G. de Vries, Nanoparticles and Catalysis, (Ed.: D. Astruc), Wiley-VCH, Weinheim, 2008, pp 303-348.
42. a) D. Morales-Morales, R. Redón, C. Yung, C. M. Jensen, Chem. Commun. 2000, 1619-1620;
43. b) J. Dupont, C. S. Consorti, J. Spencer, Chem. Rev. 2005, 105, 2527-2571;
44. c) J. G. Vries, Dalton Trans. 2006, 421-429.
45. E. Peris, J. A. Loch, J. Mata, R. H. Crabtree, Chem. Commun. 2001, 201-202.
46. K. Yu, W. Sommer, J. M. Richardson, M. Weck, C. W. Jones, Adv. Synth. Catal. 2005, 347, 161-171.
47. 2 is around €5.50. For the calculation of the costs, all prizes were taken from wellknown commercial firms (Sigma-Aldrich, VWR, etc.).
48. 2 employed in recent Suzuki-Miyaura couplings, see: a) C. Li, X.-Q. Li, C. Zhang, J. Chem. Res. 2008, 9, 525-527;
49. b) T. M. Razler, Y. Hsiao, F. Qian; R. Fu, R. K. Khan, W. Doubleday, J. Org. Chem. 2009, 74, 1381-1384.
50. a) S. Narayan, J. Muldoon, M. G. Finn, V.V. Fokin, H. C. Kolb, K. B Sharpless, Angew. Chem. 2005, 117, 3339-3343;
51. Angew. Chem. Int. Ed. 2005, 44, 3275-3279;
52. b) Y. Jung, R. A. Marcus, J. Am. Chem. Soc. 2007, 129, 5492-5502;
53. c) M. Carril, R. SanMartin, E. Domínguez, Chem. Soc. Rev. 2008, 37, 639-647.