(N-Heterocyclic Carbene)-Palladate Complexes in Anionic Mizoroki-Heck Coupling Cycles: A Combined Experimental and Computational Study

Organometallics

Volumn 34, Issue 11, 2015, Pages 2463-2470

  Guest, Daniel ^a   Menezes Da Silva, Vitor H ^b   De Lima Batista, Ana P ^b   Roe, S Mark ^a   Braga, Ataualpa A C ^b   Navarro, Oscar ^a  

^a UNIVERSITY OF SUSSEX   (United Kingdom)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CHLORINE COMPOUNDS; ORGANIC COMPOUNDS;

CATALYTIC SPECIES; CHEMICAL EQUATIONS; COMPUTATIONAL STUDIES; DFT CALCULATION; HECK COUPLING REACTION; N-HETEROCYCLIC CARBENES; QUANTITATIVE YIELDS; ROOM TEMPERATURE;

CHEMICAL REACTIONS;

EID: 84931273919     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om5012038     Document Type: Article

References (67)

1. Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320 - 2322
2. Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581
3. Oestreich, M., Ed. The Mizoroki-Heck Reaction; John Wiley & Sons: Chichester, U.K., 2009.
4. de Meijere, A.; Diederich, F., Eds.; Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; Wiley-VCH: Weinheim, Germany, 2004.
5. Phan, N. T. S.; Van Der Sluys, M.; Jones, C. W. Adv. Synth. Catal. 2006, 348, 609 - 679
6. Santos, C. I. M.; Barata, J. F. B.; Faustino, M. A.; Lodeiro, C.; Neves, M. G. P. M. S. RSC Adv. 2013, 3, 19219 - 19238
7. Whitcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 7449 - 7476
8. Kumar, A.; Rao, G. K.; Kumar, S.; Singh, A. K. Organometallics 2013, 33, 2921 - 2943
9. Knowles, J. P.; Whiting, A. Org. Biomol. Chem. 2007, 5, 31 - 44
10. Some representative examples: de Vries, J. G. Dalton Trans. 2006, 421 - 429
11. Shaw, B. L.; Perera, S. D. Chem. Commun. 1998, 1863 - 1864
12. Ruan, J.; Iggo, J. A.; Berry, N. G.; Xiao, J. J. Am. Chem. Soc. 2010, 132, 16689 - 16699
13. Montoya, V.; Pons, J.; Branchadell, V.; Garcia-Antón, J.; Solans, X.; Font-Bardía, M.; Ros, J. Organometallics 2008, 27, 1084 - 1091
14. Fiddy, S. G.; Evans, J.; Nelsius, T.; Newton, M. A.; Tsoureas, N.; Tulloch, A. A. D.; Danopoulos, A. A. Chem.-Eur. J. 2007, 13, 3652 - 3659
15. Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A.; Meyer, G. Organometallics 1995, 14, 5605 - 5614
16. This mechanism has also been suggested for soluble Pd(0) colloids or nanoparticles; see ref 3a.
17. Amatore, C.; Jutand, A. J. Organomet. Chem. 1999, 576, 254 - 278
18. Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314 - 321
19. Nolan, S. P., Ed. N-Heterocyclic Carbenes: Effective Tools for Organometallic Synthesis; Wiley-VCH: Weinheim, Germany, 2014.
20. Cazin, C. S. J., Ed. N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis; Springer Science: Heidelberg, Germany, 2011.
21. Díez-González, S., Ed. N-Heterocyclic Carbenes. From Laboratory Curiosities to Efficient Synthetic Tools; RSC Publishing: London, U.K., 2010.
22. Glorius, F., Ed. N-Heterocyclic Carbenes in Transition Metal Catalysis; Springer Science: Heidelberg, Germany, 2007.
23. Gallop, C. W. D.; Zinser, C.; Guest, D.; Navarro, O. Synlett 2014, 25, 2225 - 2228
24. Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287 - 1289
25. Chen, M.-T.; Vicic, D. A.; Turner, M. L.; Navarro, O. Organometallics 2011, 30, 5052 - 5056
26. Goggin, P. L.; Goodfellow, R. R.; Reed, F. J. S. J. Chem. Soc., Dalton Trans. 1972, 1298 - 1303
27. Duddell, D. A.; Goggin, P. L.; Goodfellow, R. J.; Norton, M. G.; Smith, J. G. J. Chem. Soc. A 1970, 545 - 564
28. Huynh, H. V.; Han, Y.; Ho, J. H. H.; Tan, G. K. Organometallics 2006, 25, 3267 - 3274
29. Hermann, W. A.; Schwarz, J.; Gardiner, M. G. Organometallics 1999, 18, 4082 - 4089
30. Heckenroth, M.; Kluser, E.; Neels, A.; Albrecht, M. Dalton Trans. 2008, 6242 - 6249
31. Zamora, M. T.; Ferguson, M. J.; McDonald, R.; Cowie, M. Dalton Trans. 2009, 7269 - 7287
32. Zamora, M. T.; Ferguson, M. J.; McDonald, R.; Cowie, M. Organometallics 2012, 31, 5463 - 5477
33. Some recent examples in the literature: Tessin, U. I.; Bantreil, X.; Songis, O.; Cazin, C. S. J. Eur. J. Inorg. Chem. 2013, 2007 - 2010
34. Gao, T.-T.; Jin, A.-P.; Shao, L.-X. Beilstein J. Org. Chem. 2012, 8, 1916 - 1919
35. Lin, Y.-C.; Hsueh, H.-H.; Kanne, S.; Chang, L.-K.; Liu, F.-C.; Lin, I. J. B. Organometallics 2013, 32, 3859 - 3869
36. Keske, E. C.; Zenkina, O. V.; Wang, R.; Crudden, C. M. Organometallics 2012, 31, 6215 - 6221
37. Pytkowicz, J.; Roland, S.; Mangeney, P.; Meyer, G.; Jutand, A. J. Organomet. Chem. 2003, 678, 166 - 179
38. Amarante, G. W.; Benassi, M.; Milagre, H.; Braga, A. A.; Maseras, F.; Eberlin, M. N.; Coelho, F. Chem.-Eur. J. 2009, 15, 12460 - 12469
39. Pérez-Rodríguez, M.; Braga, A. A. C.; Garcia-Melchor, M.; Pérez-Temprano, M. H.; Casares, J. A.; Ujaque, G.; deLera, A. R.; Álvarez, R.; Maseras, F.; Espinet, P. J. Am. Chem. Soc. 2009, 131, 3650 - 3657
40. García-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066 - 1067
41. Braga, A. A. C.; Ujaque, G.; Maseras, F. Organometallics 2006, 25, 3647 - 3658
42. García-Melchor, M.; Braga, A. A. C.; Lledós, A.; Ujaque, G.; Maseras, F. Acc. Chem. Res. 2013, 46, 2626 - 2634
43. Carrow, B. P.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 79 - 81
44. Phan, N.; VanDerSluys, M.; Jones, C. Adv. Synth. Catal. 2006, 348, 609 - 679
45. Proutiere, F.; Schoenebeck, F. Angew. Chem., Int. Ed. 2011, 50, 8192 - 8195
46. Goossen, L. J.; Koley, D.; Hermann, H. L.; Thiel, W. J. Am. Chem. Soc. 2005, 127, 11102 - 11114
47. Goossen, L. J.; Koley, D.; Hermann, H. L.; Thiel, W. Organometallics 2006, 25, 54 - 67
48. Kozuch, S.; Shaik, S.; Jutand, A.; Amatore, C. Chem.-Eur. J. 2004, 10, 3072 - 3080
49. Albert, K.; Gisdakis, P.; Rösch, N. Organometallics 1998, 17, 1608 - 1616
50. Bode, B.; Gordon, M. S. J. Mol. Graphics Mod. 1998, 16, 133 - 138
51. Bäcktorp, C.; Norrby, P.-O. J. Mol. Catal. A: Chem. 2010, 328, 108 - 113
52. Dang, Y.; Qu, S.; Wang, Z.; Wang, X. J. Am. Chem. Soc. 2014, 136, 986 - 998
53. Xu, L.; Hilton, M. J.; Zhang, X.; Norrby, P.-O.; Wu, Y.-D.; Sigman, M. S.; Wiest, O. J. Am. Chem. Soc. 2014, 136, 1960 - 1961
54. Henriksen, S. T.; Tanner, D.; Cacchi, S.; Norrby, P.-O. Organometallics 2009, 28, 6201 - 6205
55. Sköld, C.; Kleimark, J.; Trejos, A.; Odell, L. R.; Nilsson Lill, S. O.; Norrby, P.-O.; Larhed, M. Chem.-Eur. J. 2012, 18, 4714 - 4722
56. Hohenberg, P.; Kohn, W. Phys. Rev. 1964, 136, B864 - B871
57. Kohn, W.; Sham, L. J. Phys. Rev. 1965, 140, A1133 - A1138
58. Parr, R. G.; Weitao, Y. Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, USA, 1994.
59. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, M. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision D.01; Gaussian Inc.: Wallingford, CT, 2009.
60. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215 - 241
61. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157 - 167
62. Andrae, D.; Huermann, U.; Dolg, M.; Stoll, H.; Preu, H. Theor. Chim. Acta 1990, 77, 123 - 141
63. Bergner, A.; Dolg, M.; Kchle, W.; Stoll, H.; Preu, H. Mol. Phys. 1993, 80, 1431 - 1441
64. Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654 - 3665
65. Hratchian, H. P.; Schlegel, H. B. J. Chem. Theory Comput. 2005, 1, 61 - 69
66. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378 - 6396
67. Harvey, J. N. Faraday Discuss. 2010, 145, 487 - 505