Rationally designed pincer-type heck catalysts bearing aminophosphine substituents: PdIV intermediates and palladium nanoparticles

Chemistry - A European Journal

Volumn 14, Issue 26, 2008, Pages 7969-7977

  Bolliger, Jeanne L ^a   Blacque, Olivier ^a   Frech, Christian M ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

Aminophosphines; C C coupling; Nanoparticles; Palladium; Pincer reagents

Indexed keywords

PALLADIUM; PALLADIUM COMPOUNDS;

AMINOPHOSPHINES; C-C COUPLING; NANOPARTICLES; PINCER REAGENTS;

CATALYSIS;

EID: 53849148991     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800441     Document Type: Article

References (101)

1. For reviews of palladium-catalyzed Heck reaction, see: a) R. F. Heck in Palladium Reagents in Organic Syntheses (Eds.: A. R. Katritzky, O. Melh-Cohn, G W. Rees), Academic Press, London, 1985, p. 2;
2. b) R. F. Heck, "Vinyl Substitution with Organopalladium Intermediates" in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991;
3. c) J.-L. Malleron, J.-C. Fiaud, J.-Y. Legros in Handbook of Palladium-Catalysed Organic Reactions, Academic Press, London, 1997;
4. d) M. T. Reetz in Transition Metal Catalysed Reactions, (Eds.: S. G. Davies, S.-I. Murahashi), Blackwell, Oxford, 1999;
5. e) J. T. Link, L. E. Overman in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P.J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 6;
6. f) S. Bräse, A. de Meijere in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, Chapter 3.6;
7. g) K. C. Nicolaou, E. J. Sorensen in Classics in Total Synthesis, Wiley-VCH, Weinheim, 1996, Chapter 31;
8. h) R. A. de Vries, P.C. Vosejpka, M. L. Ash in Catalysis of Organic Reactions (Ed.: F. E. Herkes), M. Dekker, New York, 1998, Chapter 37;
9. i) L. F. Tietze, G. Kettschau, U. Heuschert, G. Nordmann, Chem. Eur. J. 2001, 7, 368.
10. a) M. Ohff, A. Ohff, M. E. van der Boom, D. Milstein, J. Am. Chem. Soc. 1997, 119, 11687;
11. b) K. Kiewel, Y. Liu, D. E. Bergbreiter, G. A. Sulikowski, Tetrahedron Leu. 1999, 40, 8945;
12. c) F. Miyazaki, K. Yamaguchi, M. Shibasaki, Tetrahedron Lett. 1999, 40, 7379;
13. d) D. Morales-Morales, R. Redon, C. Yung. C. M. Jensen, Chem. Commun. 2000, 1619;
14. e) D. Morales-Morales, C. Grause, K. Kasaoka, R. Redon, R. Cramer, C. M. Jensen, Inorg. Chim. Acta 2000, 300-302, 958;
15. f) S. Sjovall, O.P. Wendt, C. J. Anderson, Chem. Soc. Dalton Trans. 2002, 1396;
16. g) D. Morales-Morales, R. E. Cramer, C. M. Jensen, J. Organomet. Chem. 2002, 654, 44;
17. h) M. R. Eberhard, Org. Lett., 2004, 2125;
18. i) N. Withcombe, K. K. Hii (Mimi) S. Gibson, Tetrahedron 2001, 57, 7449.
19. a) W. A. Herrmann, C. Brossmer, K. Öfele, C. Reisinger, T. Riermeier, M. Beller, H. Fisher, Angew. Chem. 1995, 107, 1989;
20. Angew. Chem. Int. Ed. Engl. 1995, 34, 1844;
21. b) A. Linke, G. C. Fu, J. Org. Chem. 1999, 64, 10;
22. c) X. Gai, R. Grigg, I. Ramzan, V. Sridharan, S. Collard, J. Muir, Chem. Commun. 2000, 2053;
23. d) S. Gibson, D. Foster, D. Eastham, R. Tooze, D. Cole-Hamilton, Chem. Commun. 2001, 779;
24. e) M. Albrecht, G. van Koten, Angew. Chem. 2001, 113, 3866;
25. Angew. Chem. Int. Ed. 2001, 40, 3750;
26. f) M. E. van der Boom, D. Milstein, Chem. Rev. 2003, 103, 1759.
27. A. F. Linke, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 6989.
28. J. P. Stambuli, S. R. Stauffer, K. H. Shaughnessy, J. F. Hartwig, J. Am. Chem. Soc. 2001, 123, 2677.
29. a) E. Peris, J. A. Loch, J. Mata, R. H. Crabtree, Chem. Commun. 2001, 201;
30. b) S. Gründemann, M. Albrecht, J. A. Loch, J. W. Faller, R. H. Crabtree, Organometallics 2001, 20, 5485;
31. c) J. A. Loch, M. Albrecht, E. Peris, J. Mata, J. W. Faller, R. H. Crabtree, Organometallics 2002, 21, 700;
32. d) D. J. Nielsen, K. J. Cavell, B. W. Skelton, A. H. White, Inorg. Chim. Acta 2002, 327, 116;
33. e) W. A. Herrmann, V. P. W. Böhm, C. W. K. Gstöttmayr, M. Grosche, C.-P. Reisinger, T. Weskamp, J. Organomet. Chem. 2001, 617, 616;
34. f) C. Yang. H. M. Lee, S. P. Nolan, Org. Lett. 2001, 3, 1511;
35. g) N. Tsoureas, A. A. Danopoulos, A. A. D. Tulloch, M. E. Light, Organometallics 2003, 22, 4750.
36. J. L. Bolliger, O. Blacque, C. M. Frech, Angew. Chem. 2007, 119, 6634;
37. Angew. Chem. Int. Ed. 2007, 46, 6514.
38. Reviews that include catalysis of the Heck reaction by palladacycles: a) see refs [2a.b];
39. b) P. L. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009;
40. c) M. Dupont, M. Pfeffer, J. Spencer, Eur. J. Inorg. Chem. 2001, 1917;
41. d) R. B. Bedford, Chem. Commun. 2003, 1787;
42. e) G. J. de Vries, Dalton Trans. 2006, 421;
43. f) D. E. Bergbreiter, P. L. Osburn, J. D. Freis, Adv. Synth. Catal. 2005, 347, 172;
44. g) K. Yu, W. Sommer, J. M. Richardson, M. Weck, C. W. Jones, Adv. Synth. Catal. 2005, 347, 161;
45. h) K. Yu, W. Sommer, M. Week, C. W. Jones, J. Catal. 2005, 226, 101.
46. a) W. A. Herrmann, V. P. W. Böhm, C.-P. Reisinger, J. Organomet. Chem. 1999, 576, 23;
47. b) B. L. Shaw, S. D. Perera, E. A. Staley, Chem. Commun. 1998, 1362.
48. Palladium nanoparticles are proposed to be involved when phosphinite PCP-type Heck catalysts are utilized (see ref. [2f, h]). While PCP phosphinite systems might decompose at elevated temperatures and prolonged reaction times under the basic Heck conditions (probably by P-O cleavage), this is not necessarily the case for a phosphine-based PCP system.
49. The resulting catalyst solutions were used for catalytic reactions without purification and remain stable in solution for several months at room temperature, affording lhe coupling products at essentially the same conversion rates and yields as freshly prepared catalyst solutions from pure 1 and 2. respectively. The concentrations of the catalyst solutions were determined prior to use.
50. IV intermediates are involved in the catalytic cycle. The higher stability of 2 compared with 1 could provide an explanation for its lower catalytic activity if palladium nanoparticles are the active form.
51. See Experimental Section.
52. The higher reaction temperature could provide an explanation for the leveled out catalytic activity of catalysis 1 and 2, if palladium nanoparticles are the catalytically active form of lhe catalysis.
53. H. M. Lee, J. Y. Zeng, C.-H. Hu, M.-T. Lee, Inorg. Chem. 2004, 43, 6822.
54. A. H. M. de Vries, J. M. C. A. Mulders, J. H. M. Mommers, H. J. W. Henderickx, J. G. de Vries, Org. Lett. 2003, 5, 3285.
55. S. Gründemann, M. Albrecht, J. A. Loch, J. W. Faller, R. H. Crabtree, Organometallics 2001, 20, 5485.
56. a) W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Angew. Chem. 1995, 107, 2602;
57. Angew. Chem. Int. Ed. Engl. 1995, 34, 2371;
58. b) G. D. Frey, C. Reisinger, E. Herdtweck, W. A. Herrmann, J. Organomet. Chem. 2005, 690, 3193;
59. c) W A. Herrmann, K. Ofele, S. K. Schneider, E. Herdtweck, S. D. Hoffmann, Angew. Chem. 2006, 118, 3943;
60. Angew. Chem. Int. Ed. 2006, 45, 3859.
61. A. Schnyder, T. Aemmer, A. F. Indolese, U. Pittelkow, M. Studer, Adv. Synth. Catal. 2002, 344, 495.
62. The low conversion rates observed in these solvents can be explained by both, ion pair and palladium nanoparticle formation. Whilst their formation is not promoted in p-xylene. the ligating properties of DMSO could either suppress the coordination of substrate molecules at the metal centers or stabilize the catalysis, which, in turn, would retard the formation of palladium nanoparticles.
63. a) J. A. Widegren, R. G. Finke, J. Mol. Catal. A 2003, 198, 317;
64. e) C. Rocaboy, J. A. Gladysz, Org. Lett. 2002, 4, 1993;
65. b) G. M. Whitesides, M. Hackell, R. L. Brainard, J.-P. P. M. Lavalleye, A. F. Sowinski, A. N. Izumi, S. S. Moore, D. W. Brown, E. M. Staudt, Organometallics 1985, 4, 1819;
66. c) P. Foley, R. Di Cosimo, G. M. Whitesides, J. Am. Chem. Soc. 1980, 102, 6713;
67. d) D. R. Anton, R. H. Crabtree, Organometallics 1983, 2, 855.
68. It is important to note that the mercury drop test is not applicable here, since halide-exchange reactions of 1 (and 2) with bromobenzene at 100°C in DMF to form chlorobenzene and their bromo derivatives 11 (and 12) also were inhibited in the presence of mercury (for more details regarding the halide exchange, see below).
69. [9b] Waler could serve as a nucleophile, thereby explaining the shortened induction period in the presence of water. To test this possibility tetrabutylammonium bromide (ca. 15 mol%) was added to the reaction mixtures. If the mechanism would proceed according to Shaw's mechanism, the added bromide should greatly reduce the induction period. The induction period remained unchanged in the presence of added bromide, which is inconsistent with Shaw's mechanism.
70. Tetrabutylammonium bromide is known to stabilize palladium nanoparticles, See for instance a) T. Jeffery in Advances in Metal-Organic Chemistry, Vol.5 (Ed.: L.S. Liebeskind). JAI Press, Greenwich, 1996, p. 153;
71. b) M. T. Reetz, E. Weslermann, Angew. Chem. 2000, 112, 170;
72. Angew. Chem. Int. Ed. 2000, 39, 165;
73. c) A. Zapf, M. Beller, Chem. Eur. J. 2001, 7, 2908.
74. Iv intermediates are involved in the catalytic cycle: the bromide anions suppress the coordination of the substrate molecules at the metal center. On the other hand, the low concentration of palladium nanoparticles (if formed) may not need to be stabilized. In contrast, tetrabutylammonium bromide may slow down their formation and/or reduces their activity.
75. a) J. A. Widegren, R. G. Finke, J. Mol. Catal. A 2003, 198, 317;
76. b) Y. Lin, R. G. Finke, Inorg. Chem. 1994, 33, 4891;
77. c) K. S. Weddle, J. D. Aiken III, R. G. Finke, J. Am. Chem. Soc. 1998, 120, 5653.
78. [2g]
79. a) F. Shaheen, A. Badshah, M. Gielen, M. Dusek, K. Fejfarova, D. de Vos, B. Mifza, J. Organomet. Chem. 2007, 692, 3019;
80. b) F. Shaheen, A. Badshah, S. Anjum, A. Saqib, Acta Crystallogr. Sect. E 2006, 62, m329;
81. c) L. Marcheselli, C. Preti, M. Tagliazucchi, V. Cherchi, L. Sindellari, A. Furlani, A. Papaioannou, V. Scarcia, Eur. J. Med. Chem. 1993, 28, 347;
82. d) C. G. Sceney, R. Magee, J. Inorg. Nucl. Chem. 1974, 10, 323.
83. [16a,30] At higher substrate/catalyst ratios more palladium will be in the catalytic cycle. In addition, the size of the nanoparticles will be smaller at higher substrate/catalyst ratios, making the ratio between palladium on the outer rim and palladium on the inside of the particles more favorable.
84. M. T. Reetz, J. G. de Vries, Chem. Commun. 2004, 1559.
85. C. M. Frech, L. J. W. Shimon, D. Milstein, Angew. Chem. 2005, 117, 1737;
86. Angew. Chem. Int. Ed. 2005, 44, 1709.
87. C. M. Freeh, G. Leitus, D. Milstein, Organometallics 2008, 27, 894.
88. CCDC-671437 contains 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
89. 2] - a system known to form palladium nanoparticles-was used as catalyst.
90. Various catalyst concentrations were tested: 0.05. 0.02, 0.002, and 0.0005 mol % of 1 and 2, respectively.
91. A 60% conversion of 1 into 11 and a 32% conversion of 2 into 12 was observed after 5 h.
92. 2] or its dimer (possibly as a dimethylammonium salt from DMF) and exchange with the pincer complexes directly.
93. a) M. L. Clarke, D. J. Cole-Hamilton, M. Z. Slawin, J. D. Woollins, Chem. Commun. 2000, 2065;
94. b) K. G. Moloy, J. L. Peterson, J. Am. Chem. Soc. 1995, 117, 7696.
95. For example, only 10% conversion was observed in p-xylene at 100°C over night.
96. [7,13]
97. Y. Jong Gook, S. Jung Min, L. Kap Duk, K. Sangha, P. Soonheum, Bull. Korean Chem. Soc. 1996, 17, 311.
98. Full geometry optimizations were performed with the Gaussian03 program package using the mPW1PW91 functional. Computational details and a complete scheme with all calculated intermediates and transition states, simulated in different solvents is given in the Supporting Information.
99. [42]
100. [7]
101. 0 complexes was already excluded. Nevertheless, it is important to note that when styrene was used as coupling partner, a dramatic retardation in the conversion rate was observed in all cases when 1-methyl1,4-cyclohexadiene was present, implying that this test is not definitive.