A general synthetic route to mixed NHC-phosphane palladium(O) complexes (NHC = N-heterocyclic carbene)

Chemistry - A European Journal

Volumn 14, Issue 23, 2008, Pages 6987-6993

  Fantasia, Serena ^a   Nolan, Steven P ^a  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

Author keywords

N heterocyclic carbenes; Organometallic synthesis; Oxygen; Palladium; Phosphanes

Indexed keywords

PALLADIUM;

N-HETEROCYCLIC CARBENES; ORGANOMETALLIC SYNTHESIS; OXYGEN; PHOSPHANES;

PALLADIUM COMPOUNDS;

EID: 53849121992     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800815     Document Type: Article

References (43)

1. a) S. P. Nolan, N-Heterocyclic Carbenes in Synthesis, Wiley-VCH, Weinheim, 2006;
2. b) F. Glorius, Topics in Organometallics Chemistry: N-Heterocyclic Carbenes in Transition Metal Catalysis, Vol. 21, Springer, Berlin, 2007.
3. a) E. A. B. Kanlchev, C. J. O'Brien, M. G. Organ, Angew. Chem. 2007, 119, 2824-2870;
4. Angew. Chem. Int. Ed. 2007, 46, 2768-2813;
5. b) S. Díez-González, S. P. Nolan, Topics in Organometallic Chemistry 2007, pp.47-82.
6. a) D. S. McGuinness, K. J. Cavell, B. W. Skellon, A. H. White, Organometallics 1999, 18, 1596-1605;
7. b) V. P. W. Böhm, C. W. K. Gstöttmayr, T. Weskamp, W. A. Herrmann, J. Organomet. Chem. 2000, 595, 186-190;
8. c) S. Caddick, F. G. N. Cloke, G. K. B. Clenlsmith, P. B. Hitchcock, D. McKerrecher, L. R. Tilcomb, M. R. V. Williams, J. Organomet. Chem. 2001, 617-618, 635-639;
9. d) L. R. Titcomb, S. Caddick, F. G. N Cloke, D. J. Wilson, D. McKerrecher, Chem. Commun. 2001, 1388-1389;
10. e) K. Selvakumar, A. Zapf, A. Spannenberg, M. Beller, Chem. Eur. J. 2002, 8, 3901-3906;
11. f) R. Jackstell, M. Gómez Andreu, A. Frisch, K. Selvakumar, A. Zapf, H. Klein, A. Spannenberg, D. Röttger, O. Briel, R. Karch, M. Beller, Angew. Chem. 2002, 114, 1028-1031;
12. Angew. Chem. Int. Ed. 2002, 41, 986-989;
13. g) K. Selvakumar, A. Zapf, M. Beller, Org. Lett. 2002, 4, 3031-3033;
14. h) G. Altenhoff, R. Goddard, C. W. Lehmann, F. Glorius, Angew. Chem. 2003, 115, 3818-3821;
15. Angew. Chem. Int. Ed. 2003, 42, 3690-3693;
16. i) K. Arentsen, S. Caddick, F. G. N. Cloke, A. P. Herring, P. B. Hitchcock, Tetrahedron Lett. 2004, 45, 3511-3515;
17. j) K. Arentsen, S. Caddick, F. G. N. Cloke, Tetrahedron 2005, 61, 9710-9715;
18. k) J. W. Sprengers, J. Wassenaar, N. D. Clement, K. J. Cavell, C. J. Elsevier, Angew. Chem. 2005, 117, 2062-2065;
19. Angew. Chem. Int. Ed. 2005, 44, 2026-2029;
20. l) N. D. Clement, K. J. Cavell, L.-L. Ooi, Organometallics 2006, 25, 4155-4165.
21. 2] displayed very good catalytic activity: C. W. K. Gstöttmayr, V. P. W. Böhm, E. Herdtweck, M. Grosche, W. A. Herrmann, Angew. Chem. 2002, 114, 1421-1423;
22. Angew. Chem. Int. Ed. 2002, 41, 1363-1365.
23. U. Christmann, R. Vilar, Angew. Chem. 2005, 117, 370-378;
24. Angew. Chem. Im. Ed. 2005, 44, 366-374.
25. M. Matsumoto, H. Yoshioko, K. Nakatsu, T. Yoshida, S. Otsuka, J. Am. Chem. Soc. 1974, 96, 3322-3324.
26. O. Navarro, S. P. Nolan, Synthesis 2006, 366-367. [(lPr)Pd(allyl)Cl] is now commercially available from Strem and Umicore.
27. a) M. S. Viciu, R. F. Germaneau, O. Navarro-Fernandez, E. D. Stevens, S. P. Nolan, Organometallics 2002, 21, 5470-5472;
28. b) N. Marion, O. Navarro, R. A. Kelly III, S. P. Nolan, Synthesis 2003, 2590-2592;
29. c) M. S. Viciu, O. Navarro, R. F. Germaneau, R. A. Kelly III, W. Sommer, N. Marion, E. D. Stevens, S. P. Nolan, Organometallics 2004, 23, 1629-1635;
30. d) N. Marion, O. Navarro, J. Mei, E. D. Stevens, N. M. Scott, S. P. Nolan, J. Am. Chem. Soc. 2006, 128, 4101-4111;
31. e) O. Navarro, N. Marion, J. Mei, S. P. Nolan, Chem. Eur. J. 2006, 12, 5142-5148.
32. M. M. Konnick, I. A. Guzei, S. S. Stahl, J. Am. Chem. Soc. 2004, 126, 10212-10213.
33. V. S. Sergienko, M. A. Porai-Koshits, Zh. Strukt. Khim. 1987, 28,103-106.
34. Ref. [8a,8c]. For a general discussion on allyl-Pd complexes see: J. Tsuji, in Transition Metal Reagents and Catalysis, Wiley, New York, 2000.
35. A concerted o-bond methathesis mechanism might also be possible.
36. 3)Pd(allyl)Cl] see Experimental Section.
37. a) R. W. Simms, M. J. Drewitt, M. C. Baird, Organometallics 2002, 21, 2958-2963;
38. b) D. P. Allen, C. M. Crudden, L. A. Calhoun, R. Wang, J. Organomet. Chem. 2004, 689, 3203-3209.
39. 2 double bond is 1.21 Å. P. Müller, R. Herbst-Irmer, A. L. Spek, T. R. Schneider, M. R. Sawaya in Crystal Structure Refinement (Ed.: P. Müller), Oxford University Press, New York, 2006.
40. Crystallographic data tables for complexes 2, 3, and 16 could be found in the Supporting Information.
41. a) ref. 9;
42. b) N. W. Aboelella, J. T. York, A. M. Reynolds, K. Fujita, C. R. Kinsinger, C. J. Cramer, C. G. Riordan, W. B. Tolman, Chem. Commun. 2004, 1716-1717.
43. M. S. Viciu, R. F. Germaneau, O. Navarro-Fernandez, E. D. Stevens, S. P. Nolan, Organometallics 2002, 21, 5470-5472.