A DFT study of site-selectivity in oxidative addition reactions with Pd0 complexes: The effect of an azine nitrogen and the use of different types of halogen atoms in the substrate

European Journal of Organic Chemistry

Volumn , Issue 16, 2010, Pages 3152-3158

  Herrebout, Wouter A ^a   Nagels, Nick ^a   Verbeeck, Stefan ^a   Van Der Veken, Benjamin J ^a   Maes, Bert U W ^a  

^a UNIVERSITY OF ANTWERP   (Belgium)

Author keywords

Density functional calculations; Oxidative addition; Palladium; Selectivity

Indexed keywords

EID: 77952589169     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900808     Document Type: Article

References (56)

1. Palladium in Organic Synthesis (Ed.: J. Tsuji), vol.14, Springer, Dordrecht, 2005.
2. For recent books dealing with the synthesis and construction of heterocycles via Pd-catalysis see: a) Palladium in Heterocyclic Chemistry (Eds.: 11 Li, G. W. Gribble), vol.26 Pergamon, Amsterdam, 2006;
3. b) A. Kotschy, G. Timári, Heterocycles from Transition Metal Catalysis (Eds.: B. James, P. W. N. M. van Leeuwen), vol.28, Springer, Dordrecht, 2005.
4. a) S. L. Buchwald, C. Mauger, G. Mignani, U. Scholz, Adv. Synth. Catal. 2006, 348, 23-31;
5. b) J. P. Corbet, G. Mignani, Chem. Rev. 2006, 106, 2651-2710;
6. (c) H.-U. Blaser, A. Indolese, F. Naud, U. Nettekoven, A. Schnyder, Adv. Synth. Catal. 2004, 346, 1583-1598;
7. (d) A.M. Rouhi, Chem. Eng. News 2004, 82, 49-58;
8. e) C. Torborg, M. Beller, Adv. Synth. Catal. 2009, 351, 3027-3043.
9. 0 see: a) R. Fazaeli, A. Ariafard, S. Jamshidi, E. S. Tabatabaie, K. A. Pishro, J. Organomet. Chem. 2007, 692, 3984-3993;
10. b) K. C. Lam, T. D. Marder, Z. Lin, Organometallics 2007, 26, 758-760;
11. (c) M. Ahlquist, P.-O. Norrby, Organometallics 2007, 26, 550-553;
12. (d) M. Ahlquist, P. Fristrup, D. Tanner, P.-O. Norrby, Organometallics 2006, 25, 2066-2073;
13. e) A. Ariafard, Z. Lin, Organometallics 2006, 25, 4030-4033;
14. f) L. J. Goossen, D. Koley, H. Hermann, W. Thiel, Organometallics 2005, 24, 2398-2410;
15. g) L. J. Goossen, D. Koley, H. Hermann, W. Thiel, Chem. Commun. 2004, 2141-2143;
16. h) U.M. Senn, T. Ziegler, Organometallics 2004, 23, 2980-2988.
17. a) I. J. S. Fairlamb, C. T. O'Brien, Z. Lin, K. C. Lamb, Org. Biomol. Chem. 2006, 4, 1213-1216;
18. b) C. Y. Legault, Y. Garcia, C. A. Merlic, J. Am. Chem. Soc. 2007, 129, 12664-12665.
19. a) I. J. S. Fairlamb, Chem. Soc. Rev. 2007, 36, 1036-1045;
20. b) S. Schroter, C. Stock, T. Bach, Tetrahedron 2005, 61, 2245-2267.
21. 2,3-Dichloropyridine: T. H. M. Jonckers, B. U. W. Maes, G. L. F. Lemière, R. Dommisse, Tetrahedron 2001, 57, 7027-7034.
22. 2-Chloro-3-iodopyridine: a) B. U. W. Maes, K. T. J. Loones, T. H. M. Jonckers, G. L. F. Lemière, R. A. Dommisse, A. Haemers, Synlett 2002, 1995-1998;
23. b) C. Meyers, B. U. W. Maes, K. T. J. Loones, G. Bal, G. L. F. Lemière, R. A. Dommisse, J. Org. Chem. 2004, 69, 6010-6017;
24. (c) K. T. J. Loones, B. U.W. Maes, R. A. Dommisse, G. L. F. Lemière, Chem. Commun. 2004, 2466-2467;
25. (d) G. Rombouts, B.U.W. Maes, T. H. M. Jonckers, K. T. J. Loones, Org. Synth. 2007, 84, 215-221.
26. 2,3-Dibromopyridine: K. T. J. Loones, B. U. W. Maes, C. Meyers, J. Deruytter, J. Org. Chem. 2006, 71, 260-264.
27. For 2,3-Dichloropyridine see for example: a) D. Najiba, J.-F. Carpentier, Y. Castanet, C. Biot, J. Brocard, A. Mortreux, Tetrahedron Lett. 1999, 40, 3719-3722;
28. b) D. R. Gauthier, R. H. Szumigala, P. G. Dormer, J. D. Armstrong, R. P. Volante, P. J. Reider, Org. Lett. 2002, 4, 375-378;
29. (c) N. M. Simkovsky, M. Ermann, S. M. Roberts, D. M. Parry, A. D. Baxter, J. Chem. Soc. Perkin Trans. 1 2002, 1847-1849;
30. (d) C. S. Burgey, K. A. Robinson, T. A. Lyle, P. E. J. Sanderson, S. D. Lewis, B. J. Lucas, J. A. Kreuger, R. Singh, C. Miller-Stein, R. B. White, B. Wong, E. A. Lyle, P. D. Williams, C. A. Coburn, B. D. Dorsey, J. C. Barrow, M. T. Stranieri, M. A. Holalian, G. R. Sitko, J. J. Cook, D. R. McMasters, C. M. McDonough, W. M. Sanders, A. A. Wallace, F. C. Clayton, D. Bohn, Y. M. Leonard, T. J. Detwiler, J. J. Lynch, Y. Yan, Z. Chen, L. Kuo, S. J. Gardell, J. A. Shafer, J. P. Vacca, J. Med. Chem. 2003, 46, 461-473;
31. e) E. Maerten, F. Hassouna, S. Couve-Bonnaire, A. Mortreux, J.F. Carpentier, Y. Castanet, Synlett 2003, 1874-1876;
32. f) J. Albaneze-Walker, C. Bazaral, T. Leavey, P. G. Dormer, J. A. Murry, Org. Lett. 2004, 6, 2097-2100;
33. g) E. Maerten, M. Sauthier, A. Mortreux, Y. Castanet, Tetrahedron 2007, 63, 682-689;
34. h) B. H. Lipshutz, A. R. Abela, Org. Lett. 2008, 10, 5329-5332. For 2-chloro-3-iodopyridine see for example:
35. (i) F. Cottet, M. Schlosser, Eur. J. Org. Chem. 2002, 327-330;
36. j) J. Dix, C. Doll, H. Hopf, P. G. Jones, Eur. J. Org. Chem. 2002, 2547-2556;
37. k) A. Bouillon, A. S. Voisin, A. Robic, J.-C. Lancelot, V. Collot, S. Rault, J. Org. Chem. 2003, 68, 10178-10180;
38. (l) J. Liu, A. E. Fitzgerald, N.S. Maní, J. Org. Chem. 2008, 73, 2951-2954. For 2,3-dibromopyridine see for example:
39. (m) M. Carril, R. SanMartin, E. Domínguez, I. Tellitu, Tetrahedron 2007, 63, 690-702;
40. n) S. T. Handy, T. Wilson, A. Muth, J. Org. Chem. 2007, 72, 8496-8500.
41. For a recent example of all atom DFT calculations involving transition metal complexes consisting of BINAP and XANTPHOS, respectively, see: a) T. Leyssens, D. Peeters, J. N. Harvey, Organometallics 2008, 27, 1514-1523;
42. b) J. D. Hicks, A. M. Hyde, A. M. Cuezva, S. L. Buchwald, J. Am. Chem. Soc. 2009, 131, 16720-16734.
43. For an example in which the crucial role of the selection of a pliosphane model for rhodium catalysts in hydroformylation reactions has been shown see: M. Torrent, M. Sola, G. Frenking, Chem. Rev. 2000, 100, 439-493.
44. M. J. Frisch, G.W. Trucks, H.B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Clieeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Parkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresrnan, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, J. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laliam, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision C02, Gaussian, Inc., Wallingford CT, 2004.
45. a) C. Peng, H. B. Schlegel, Isr. J. Chem. 1993, 33, 449-454;
46. b) C. Peng, P. Y. Ayala, H. B. Schlegel, M. J. Frisch, J. Comput. Chem. 1996, 17, 49-56.
47. [151 A. Schäfer, H. Horn, R. Ahlrichs, J. Chem. Phys. 1992, 97, 2571-2577.
48. a) A. Schäfer, C. Huber, R. Ahlrichs, J. Chem. Phys. 1994, 100, 5829-5835;
49. b) F. Weigend, R. Ahlrichs, Phys. Chem. Chem. Phys. 2005, 7, 3297-3305.
50. S. Grimme, J. Comput. Chem. 2006, 27, 1787-1799.
51. a) R. Ahlrichs, M. Baer, M. Haeser, H. Horn, C. Koelmel, Chem. Phys. Lett. 1989, 162, 165-169;
52. b) M. Arnim, R. Ahlrichs, J. Comput. Chem. 1998, 19, 1746-1757.
53. M. Sierka, A. Hogekamp, R. Ahlrichs, J. Chem. Phys. 2003, 118, 9136-9148.
54. S. Kozuch, C. Amatore, A. Jutand, S. Shaik, Organometallics 2005, 24, 2319-2330.
55. M. Brookhart, M. L. H. Green, G. Parkin, Proc. Natl. Acad. Sci. USA 2007, 104, 6908-6914.
56. 3 and palladium-iodine bonding for the bidentate ligands.