Design of cationic mixed phosphine/n-heterocyclic carbene palladium(ii) π Allyl complexes as monoligated phosphine Pd(0) precatalysts: Synthesis, structural studies, catalysis, and reactivity

Organometallics

Volumn 27, Issue 24, 2008, Pages 6507-6520

  Normand, Adrien T ^a   Stasch, Andreas ^a   Ooi, Li Ling ^a   Cavell, Kingsley J ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINE COMPOUNDS; DYES; ETHYLENE; PALLADIUM; PHOSPHORUS COMPOUNDS;

ACTIVE SPECIES; ALLYL COMPLEXES; ALLYL GROUPS; CARBENE; IMIDAZOLIUM SALTS; PERPENDICULAR ORIENTATIONS; PHOSPHINE LIGANDS; PRE-CATALYSTS; REDUCTIVE ELIMINATIONS; STRUCTURAL STUDIES; TERTIARY PHOSPHINES;

PALLADIUM COMPOUNDS;

EID: 61849130155     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om8008052     Document Type: Article

References (107)

1. Aakermark, B.; Krakenberger, B.; Hansson, S.; Vitagliano, A. Organometallics 1987, 6, 620-628.
2. Torralba, M. C.; Campo, J. A.; Heras, J. V.; Bruce, D. W.; Cano, M. Dalton Trans. 2006, 3918-3926.
3. Johns, A. M.; Tye, J. W.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 16010-16011.
4. Auburn, P. R.; Mackenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033-2046.
5. Bastero, A.; Bella, A. F.; Fernández, F.; Jansat, S.; Claver, C.; Gómez, M.; Muller, G.; Ruiz, A.; Font-Bardía, M.; Solans, X. Eur. J. Inorg. Chem. 2007, 132-139.
6. Schott, D.; Pregosin, P. S.; Veiros, L. F.; Calhorda, M. J. Organometallics 2005, 24, 5710-5717.
7. Ding, Y.; Goddard, R.; Pörschke, K.-R. Organometallics 2005M, 24, 439-445.
8. Chernyshova, E. S.; Goddard, R.; Pörschke, K. R. Organometallics 2007, 26, 3236-3251.
9. Filipuzzi, S.; Pregosin, P. S.; Albinati, A.; Rizzato, S. Organometallics 2008, 27, 437-444.
10. Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257-276.
11. Fairlamb, I. J. S.; Lloyd-Jones, G. C.; Vyskocil, Š.; Kocovský, P. Chem.-Eur. J. 2002, 8, 4443-4453.
12. Faller, J. W.; Sarantopoulos, N. Organometallics 2004, 23, 2179-2185.
13. Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921-2944.
14. Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
15. Pregosin, P. S.; Salzmann, R. Coord. Chem. Rev. 1996, 155, 35-68.
16. Abbenhuis, H. C. L.; Burckhardt, U.; Gramlich, V.; Koellner, C.; Pregosin, P. S.; Salzmann, R.; Togni, A. Organometallics 1995, 14, 759-766.
17. Sprinz, J.; Kiefer, M.; Helmchen, G.; Reggelin, M.; Huttner, G.; Walter, O.; Zsolnai, L. Tetrahedron Lett. 1994, 35, 1523-1526.
18. Dotta, P.; Kumar, P. G. A.; Pregosin, P. S. Magn. Reson. Chem. 2002, 40, 653-658.
19. Markert, C.; Neuburger, M.; Kulicke, K.; Meuwly, M.; Pfaltz, A, Angew. Chem., Int. Ed. 2007, 46, 5892-5895.
20. Trost, B. M. Proc. Natl. Acad. Sci. 2004, 101, 5348-5355.
21. Pfaltz, A.; Drury, W. J. D., III. Proc. Natl. Acad. Sci. 2004, 101, 5723-5726.
22. Halpern, J.; Trost, B. M. Proc. Natl. Acad. Sci. 2004, 101, 5347.
23. Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336-345.
24. Albinati, A.; Ammann, C.; Pregosin, P. S. Organometallics 1990, 9, 1826-1833.
25. Breutel, C.; Pregosin, P. S.; Salzmann, R.; Togni, A. J. Am. Chem. Soc. 1994, 116, 4067-4068.
26. Herrmann, J.; Pregosin, P. S.; Salzmann, R.; Albinati, A. Organometallics 1995, 14, 3311-3318.
27. Viviente, E. M.; Pregosin, P. S.; Schott, D. NMR spectroscopy and homogeneous catalysis. In Mechanisms in Homogeneous Catalysis; Heaton, B., Ed.; Wiley-VCH: Weinheim, 2005; pp 1-80.
28. Filipuzzi, S.; Pregosin, P. S.; Albinati, A.; Rizzato, S. Organometallics 2006, 25, 5955-5964.
29. McGuinness, D. S.; Cavell, K. J. Organometallics 2000, 19,4918-4920.
30. McGuinness, D. S.; Saendig, N.; Yates, B. F.; Cavell, K. J. J. Am. Chem. Soc. 2001, 123, 4029-4040.
31. Cavell, K. J.; McGuinness, D. S. Coord. Chem. Rev. 2004, 248, 671-679.
32. Bacciu, D.; Cavell, K. J.; Fallis, I. A.; Ooi, L.-l. Angew. Chem., Int. Ed. 2005, 44, 5282-5284.
33. Graham, D. C.; Cavell, K. J.; Yates, B. F. Dalton Trans. 2005, 1093-1100.
34. Graham, D. C.; Cavell, K. J.; Yates, B. F. Dalton Trans. 2006, 1768-1775.
35. Nielsen, D. J.; Cavell, K. J.; Skelton, B. W.; White, A. H. Inorg. Chim. Acta 2006, 359, 1855-1869.
36. Magill, A. M.; Yates, B. F.; Cavell, K. J.; Skelton, B. W.; White, A. H. Dalton Trans. 2007, 3398-3406.
37. The term "monoligated" is somewhat inaccurate, as it is likely that 2-propenylimidazolium would bind, albeit weakly, to the Pd(0) phosphine complex.
38. Christmann, U.; Vilar, R. Angew. Chem., Int. Ed. 2005, 44, 366-374.
39. Zapf, A.; Beller, M. Chem. Commun. 2005, 431-440.
40. Kackstell, R.; Harkal, S.; Jiao, H.; Spannenberg, A.; Borgmann, C.; Röttger, D.; Nierlich, F.; Elliot, M.; Niven, S.; Cavell, K. J.; Navarro, O.; Viciu, M. S.; Nolan, S. P.; Beller, M. Chem.-Eur. J. 2004, 10, 4661-4670.
41. Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem.-Eur. J. 2002, 8, 3901-3906.
42. Andreu, M. G.; Zapf, A.; Beller, M. Chem. Commun. 2000, 2475-2476.
43. Viciu,.M. S.; Germaneau, R. F.; Navarro-Fernandez, O.; Stevens, E. D.; Nolan, S. P. Organometallics 2002, 21, 5470-5472.
44. Viciu, M. S.; Kissling, R. M.; Stevens, E. D.; Nolan, S. P. Org. Lett. 2002, 4, 2229-2231.
45. Viciu, M. S.; Kelly, R. A., III; Stevens, E. D.; Naud, F.; Studer, M.; Nolan, S. P. Org. Lett. 2003, 5, 1479-1482.
46. Marion, N.; Ecarnot, E. C.; Navarro, O.; Amoroso, D.; Bell, A.; Nolan, S. P. J. Org. Chem. 2006, 71, 3816-3821.
47. Marion, N.; Navarro, O.; Mei, J.; Stevens, E. D.; Scott, N. M.; Nolan, S. P. J. Am. Chem. Soc. 2006, 128, 4101-4111.
48. Navarro, O.; Marion, N.; Mei, J.; Nolan, S. P. Chem.-Eur. J. 2006, 12, 5142-5148.
49. Biscoe, M. R.; Fors, B. P.; Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 6686-6687.
50. Valente, C.; Baglione, S.; Candito, D.; O'Brien, C. J.; Organ, M. G. Chem. Commun. 2008, 735-737.
51. Organ, M. G.; Abdel-Hadi., M.; Avola, S.; Dubovyk, I.; Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Sayah, M.; Valente, C. Chem.-Eur. J. 2008, 14, 2443-2452.
52. Organ, M. G.; Avola, S.; Dubovyk, I.; Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Valente, C. Chem.-Eur. J. 2006, 12, 4749-4755.
53. O'Brien, C. J.; Kantchev, E. A. B.; Valente, C.; Hadei, N.; Chass, G. A.; Lough, A.; Hopkinson, A. C.; Organ, M. G. Chem.-Eur. J. 2006, 12, 4743-4748.
54. Viciu, M. S.; Navarro, O.; Germaneau, R. F.; Kelly, R. A., III; Sommer, W.; Marion, N.; Stevens, E. D.; Cavallo, L.; Nolan, S. P. Organometallics 2004, 23, 1629-1635.
55. Viciu, M. S.; Zinn, F. K.; Stevens, E. D.; Nolan, S. P. Organometallics 2003, 22, 3175-3177.
56. Maion, N.; Frémont, P. d.; Puijk, I. M.; Ecarnot, E. C.; Amoroso, D.; Bell, A.; Nolan, S. P. Adv. Synth. Catal. 2007, 349, 2380-2384.
57. Navarro, O.; Nolan, S. Synthesis 2006, 366-367.
58. Fantasia, S.; Nolan, S. P. Chem.-Eur. J. 2008, 14, 6987-6993.
59. Bonnet, L. G.; Douthwaite, R. E.; Kariuki, B. M. Organometallics 2003, 22, 4187-4189.
60. Roseblade, S. J.; Ros, A.; Monge, D.; Alcarazo, M.; Alvarez, E.; Lassaletta, J. M.; Fernandez, R. Organometallics 2007, 26, 2570-2578.
61. Toselli, N.; Martin, D.; Buono, G. Org. Lett. 2008, 10, 1453-1456.
62. Roland, S.; Audouin, M.; Mangeney, P. Organometallics 2004, 23, 3075-3078.
63. Peng, H. M.; Song, G.; Li, Y.; Li,'X. Inorg. Chem. 2008, 47. 8031-8043.
64. Ren, H.; Yao, P.; Xu, S.; Song, H.; Wang, B. J. Organomet. Chem. 2007, 692, 2092-2098.
65. Danopoulos, A. A.; Tsoureas, N.; Macgregor, S. A.; Smith, C. Organometallics 2007, 26, 253-263.
66. Barczak, N. T.; Grote, R. E.; Jarvo, E. R. Organometallics 2007, 26, 4863-4865.
67. Visentin, F.; Togni, A. Organometallics 2007, 26, 3746-3754.
68. Flahaut, A.; Roland, S.; Mangeney, P. J. Organomet. Chem. 2007, 692, 5754-5762.
69. Wang, C.-Y.; Liu, Y.-H.; Peng, S.-M.; Chen, J.-T.; Liu. S.-T. J. Organomet. Chem. 2007, 692, 3976-3983.
70. DiRenzo, G. M.; White, P. S.; Brookhart, M. J Am. Chem. Soc. 1996, 118, 6225-6234.
71. Tolman, C. A. Chem. Rev. 1977, 77, 313-348.
72. Hills, I. D.; Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5749-5752.
73. Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295-4298.
74. Kudo, N.; Perseghini, M.; Fu, G. C. Angew. Chem., Int. Ed. 2006, 45, 1282-1284.
75. Netherton, M. R.; Dai, C.; Neuschutz, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 10099-10100.
76. A Tolman map of the ligands in this work can be found in the Supporting Information.
77. However, an impure sample of 7a was successfully recrystallized from DCM/hexane on a small scale, and crystals suitable for X-ray diffraction were obtained.
78. 31P NMR spectroscopy and ESI-MS.
79. 3 onto the allyl ligand and indicates that NHC ligands are probably far better at labilizing the chloro ligand (and slow down the nucleophilic attack on the allyl).
80. Reference deleted in revision.
81. Some compounds did not crystallize; others gave thin microcrystals unsuitable for X-ray crystallography.
82. 4 anions have been omitted from these projections for clarity. Thermal ellipsoids are drawn at the 50% probability level.
83. Comprising the three carbon atoms coordinated to Pd.
84. Comprising Pd and the four atoms sitting at the corners of the pseudo-square.
85. Comprising the three carbon and two nitrogen atoms of the imidazolin-2-ylidene ring.
86. These angles were calculated with the PLATON suite of programs using the LSPL and CALC GEOM commands.
87. Cl is relatively small, but the fact that smaller NHCs significantly deviate from this orientation points to a steric rather than electronic preference.
88. Cordero, B.; Gómez, V.; Platero-Prats, A. E.; Revés, M.; Echeverría, J.; Cremades, E.; Barragán, F.; Alvarez, S. Dalton Trans. 2008, 2832-2838.
89. Clarke, M. L.; Ellis, D.; Mason, K. L.; Orpen, A. G.; Pringle, P. G.; Wingad, R. L.; Zaher, D. A.; Baker, R. T. Dalton Trans. 2005, 1294-1300.
90. Some peaks are visible depending on the zoom applied to the spectra, but they disappear when all the circled peaks are visible.
91. Normand, A. T., Yen, S. K.; Huynh, H. V.; Hor, T. S. A.; Cavell, K. J. Organometallics 2008, 27, 3153-3160.
92. Normand, A. T.; Hawkes, K. J.; Clement, N. D.; Cavell, K. J.; Yates, B. F. Organometallics 2007, 26, 5352-5363.
93. Clement, N. D.; Cavell, K. J. Angew. Chem., Int. Ed. 2004, 43, 3845-3847.
94. Eventually, we did not find any benefit in using Pd catalysts. In particular, isomerizable and/or electron-withdrawing olefins did not react.
95. ESI-MS of 4b does not show the presence of 2-propenyltetram- ethylimidazolium in the absence of heating; therefore its presence cannot be attributed to MS-induced reductive elimination.
96. Nielsen, D. J.; Cavell, K. J., Pd-NHC Complexes as Catalysts in Telomerization and Aryl Amination Reactions. In N-Heterocyclic Carbenes in Synthesis; Nolan, S. P., Ed.; Wiley-VCH Verlag GmbH & Co.: Weinheim, 2006; pp 73-102.
97. Farina, V. Adv. Synth. Catal. 2004, 346, 1553-1582.
98. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066.
99. McGuinness, D. S.; Cavell, K. J.; Skelton, B. W.; White, A. H. Organometallics 1999, 18, 1596-1605.
100. Ozawa, F.; Hidaka, T.; Yamamoto, T.; Yamamoto, A. J. Organomet. Chem. 1987, 330, 253-263.
101. Ozawa, F.; Fujimori, M.; Yamamoto, T.; Yamamoto, A. Organometallics 1986, 5, 2144-2149.
102. Cardenas, D. J.; Martin-Matute, B.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 5033-5040.
103. Chen, W.; Liu, F. J. Organomet. Chem. 2003, 673, 5-12.
104. Kuhn, N.; Kratz, T. Synthesis 1993, 561-562.
105. Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. J. Org. Chem. 1997, 62, 7512-7515.
106. Tinkl, M.; Hafner, A. WO 9947474, 1999.
107. Tinkl, M.; Hafner, A. WO 2001016057, 2001.