Reduction of a chelating bis(NHC) palladium(II) complex to [{μbis( NHC)}2Pd2H]+: A terminal hydride in a binuclear palladium(I) species formed under catalytically relevant conditions

Angewandte Chemie - International Edition

Volumn 49, Issue 36, 2010, Pages 6315-6318

  Boyd, Peter D W ^a,e   Edwards, Alison J ^b   Gardiner, Michael G ^a   Ho, Curtis C ^a   Lemée Cailleau, Marie Hélène ^c   McGuinness, David S ^a   Riapanitra, Anung ^a,f   Steed, Jonathan W ^d   Stringer, Damien N ^a   Yates, Brian F ^a  

^a UNIVERSITY OF TASMANIA   (Australia)

^b AUSTRALIAN NUCLEAR SCIENCE AND TECHNOLOGY ORGANISATION   (Australia)

^c INSTITUT LAUE LANGEVIN   (France)

^d DURHAM UNIVERSITY   (United Kingdom)

^e UNIVERSITY OF AUCKLAND   (New Zealand)

^f Universitas Jenderal Soedirman ^*  (India)

Author keywords

Coupling reactions; Homogeneous catalysis; N heterocyclic carbenes; Palladium; Reduction

Indexed keywords

COUPLING REACTION; CRYSTAL STRUCTURE DETERMINATION; FLUXIONAL BEHAVIOR; HIGH YIELD; HOMOGENEOUS CATALYSIS; N-HETEROCYCLIC CARBENE COMPLEX; N-HETEROCYCLIC CARBENES; PALLADIUM COMPLEXES; PALLADIUM PRECURSORS;

CARBON INORGANIC COMPOUNDS; CATALYSIS; CRYSTAL STRUCTURE; ORGANIC COMPOUNDS; PALLADIUM; REACTION KINETICS;

PALLADIUM COMPOUNDS;

EID: 77956024615     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201003177     Document Type: Article

References (62)

1. W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Angew. Chem. 1995, 107, 2602-2605
2. Angew. Chem. Int. Ed. Engl. 1995, 34, 2371-2374
3. S. Díez-González, N. Marion, S. P. Nolan, Chem. Rev. 2009, 109, 3612-3676.
4. E. A. B. Kantchev, C. J. O'Brien, M. G. Organ, Angew. Chem. 2007, 119, 2824-2870
5. Angew. Chem. Int. Ed. 2007, 46, 2768-2813
6. N. Marion, S. P. Nolan, Acc. Chem. Res. 2008, 41, 1440-1449.
7. D. S. McGuinness, K. J. Cavell, B. F. Yates, B. W. Skelton, A. H. White, J. Am. Chem. Soc. 2001, 123, 8317-8328.
8. K. J. Cavell, D. S. McGuinness, Coord. Chem. Rev. 2004, 248, 671-681
9. V. Farina, Adv. Synth. Catal. 2004, 346, 1553-1582
10. Z. Fei, D. Zhao, D. Pieraccini, W. H. Ang, T. J. Geldbach, R. Scopelliti, C. Chiappe, P. J. Dyson, Organometallics 2007, 26, 1588-1598.
11. P. L. Arnold, M. S. Sanford, S. M. Pearson, J. Am. Chem. Soc. 2009, 131, 13912-13913.
12. J. C. Green, R. G. Scurr, P. L. Arnold, F. G. N. Cloke, Chem. Commun. 1997, 1963-1964
13. D. S. McGuinness, K. J. Cavell, B.W. Skelton, A. H. White, Organometallics 1999, 18, 1596-1605.
14. 3 clusters have recently been reported by potassium graphite reduction of palladium(II) precursors: C. E. Ellul, M. F. Mahon, M. K.Whittlesey, J. Organomet. Chem. 2010, 695, 6-10.
15. M. G. Gardiner,W. A. Herrmann, C.-P. Reisinger, J. Schwarz, M. Spiegler, J. Organomet. Chem. 1999, 572, 239-247
16. T. Scherg, S. K. Schneider, G. D. Frey, J. Schwarz, E. Herdtweck, W. A. Herrmann, Synlett 2006, 18, 2894-2907.
17. int=0.130). CCDC 778437, CCDC 778438, CCDC 778439, CCDC 778440, and CCDC 778441 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
18. M. Portnoy, F. Frolow, D. Milstein, Organometallics 1991, 10, 3960-3962.
19. S. J. Young, B. Kellenberger, J. H. Reibenspies, S. E. Himmel, M. Manning, O. P. Anderson, J. K. Stille, J. Am. Chem. Soc. 1988, 110, 5744-5753.
20. For Ge, see: M. Tanabe, N. Ishikawa, K. Osakada, Organometallics 2006, 25, 796-798, and references therein for earlier Si and P examples.
21. M. M. Konnick, B. A. Gandhi. I. A. Guzei, S. S. Stahl, Angew. Chem. 2006, 118, 2970-2973
22. Angew. Chem. Int. Ed. 2006, 45, 2904-2907.
23. N. D. Clement, K. J. Cavell, C. Jones, C. J. Elsevier, Angew. Chem. 2004, 116, 1297-1299
24. Angew. Chem. Int. Ed. 2004, 43, 1277-1279
25. T. Steinke, B. K. Shaw, H. Jong, B. O. Patrick, M. D. Fryzuk, Organometallics 2009, 28, 2830-2836.
26. 2-linked bis(NHC) example: K. A. Kreisel, G. P. A. Yap, K. H. Theopold, Chem. Commun. 2007, 1510-1511
27. for a review, see: M. Poyatos, J. A. Mata, E. Peris, Chem. Rev. 2009, 109, 3677-3707.
28. T. Murahashi, H. Kurosawa, Coord. Chem. Rev. 2002, 231, 207-228
29. T. Murahashi, T. Otani, E. Mochizuki, Y. Kai, H. Kurosawa, J. Am. Chem. Soc. 1998, 120, 4536-4537
30. S. Deeken, G. Motz, V. Bezugly, H. Borrmann, F. R. Wagner, R. Kempe, Inorg. Chem. 2006, 45, 9160-9162.
31. Full DFT geometry optimizations using the Gaussian 09 program with the density functionals B3LYP and wB97X with a SDD pseudopotential/basis set for Pd and D95 basis set for C, H, and N. Further computational details are given in the Supporting Information.
32. II complex is known: C. M. Frech, L. J. W. Shimon, D. Milstein, Angew. Chem. 2005, 117, 1737-1739
33. Angew. Chem. Int. Ed. 2005, 44, 1709-1711.
34. M. S. Viciu, G. A. Grasa, S. P. Nolan, Organometallics 2001, 20, 3607-3612.
35. Y. A. Wanniarachchi, M. A. Khan, L. M. Slaughter, Organometallics 2004, 23, 5881-5884.
36. C. A. Quezada, J. C. Garrison, M. J. Panzner, C. A. Tessier, W. J. Youngs, Organometallics 2004, 23, 4846-4848
37. D. Q. Wang, Acta Crystallogr. Sect. E 2006, 62, m1565-1566.
38. S. S. Subramanium, L. M. Slaughter, Dalton Trans. 2009, 6930-6933.
39. M. Poyatos, M. Sanaffl, E. Peris, Inorg. Chem. 2003, 42, 2572-2576.
40. M. A. Taige, A. Zeller, S. Ahrens, S. Goutal, E. Herdtweck, T. Strassner, J. Organomet. Chem. 2007, 692, 1519-1529.
41. G. Bertrand, E. Díez-Barra, J. Fernández-Baeza, H. Gornitzka, A. Moreno, A. Otero, R. Rodríguez-Curiel, J. Tejeda, Eur. J. Inorg. Chem. 1999, 1965-1971
42. C. Tubaro, A. Biffis, C. Gonzato, M. Zecca, M. Basato, J. Mol. Catal. A 2006, 248, 93-98
43. M. Heckenroth, A. Neels, H. Stoeckli-Evans,M. Albrecht, Inorg. Chim. Acta 2006, 359, 1929-1938.
44. See, for example: J. P. Stambuli, R. Kuwano, J. F. Hartwig, Angew. Chem. 2002, 114, 4940-4942
45. Angew. Chem. Int. Ed. 2002, 41, 4746-4748
46. M. Prashad, X. Y. Mak, Y. Liu, O. Repic, J. Org. Chem. 2003, 68, 1163-1164
47. U. Christmann, R. Vilar, A. J. P. White, D. J. Williams, Chem. Commun. 2004, 1294-1295
48. H. Weissman, L. J. W. Shimon, D. Milstein, Organometallics 2004, 23, 3931-3940
49. U. Christmann, D. A. Pantazis, J. Benet-Buchholz, J. E. McGrady, F. Maseras, R. Vilar, J. Am. Chem. Soc. 2006, 128, 6376-6390
50. S. E. Denmark, J. D. Baird, Org. Lett. 2006, 8, 793-795
51. T. E. Barder, J. Am. Chem. Soc. 2006, 128, 898-904
52. X. Han, Z. Weng, T. S. A. Hor, J. Organomet. Chem. 2007, 692, 5690-5696.
53. D. C. Powers, M. A. L. Geibel, J. E. M. N. Klein, T. Ritter, J. Am. Chem. Soc. 2009, 131, 17050-17051
54. A. J. Canty, Dalton Trans. 2009, 10409-10417
55. A. J. Canty, M. G. Gardiner, R. C. Jones, T. Rodemann, M. Sharma, J. Am. Chem. Soc. 2009, 131, 7236-7237
56. D. C. Powers, T. Ritter, Nat. Chem. 2009, 1, 302-309
57. G. L. Hamilton, F. D. Toste, Nature 2009, 459, 917-918
58. G. L. Hamilton, F. D. Toste, Nature 2009, 459, 917-918 N. R. Deprez, M. S. Sanford, J. Am. Chem. Soc. 2009, 131, 11234-11241.
59. M. Tromp, J. R. A. Sietsma, J. A. van Bokhoven, G. P. F. van Strijdonck, R. J. van Haaren, A. M. J. van der Eerden, P.W. N. M. van Leeuwen, D. C. Koningsberger, Chem. Commun. 2003, 128-129.
60. C. Markert, M. Neuburger, K. Kulicke, M. Meuwly, A. Pfaltz, Angew. Chem. 2007, 119, 5996-5999
61. Angew. Chem. Int. Ed. 2007, 46, 5892-5895.
62. T. M. McPhillips, S. E. McPhillips, H. J. Chiu, A. E. Cohen, A. M. Deacon, P. J. Ellis, E. Garman, A. Gonzalez, N. K. Sauter, R. P. Phizackerley, S. M. Soltis, P. Kuhn, J. Synchrotron Rad. 2002, 9, 401-406.