DFT-based insights into Pd-Zn cooperative effects in oxidative addition and reductive elimination processes relevant to Negishi cross-couplings

Organometallics

Volumn 31, Issue 5, 2012, Pages 2053-2058

  González Pérez, Adán B ^a   Álvarez, Rosana ^a   Faza, Olalla Nieto ^a   De Lera, Ángel R ^a   Aurrecoechea, José M ^b  

^a UNIVERSITY OF VIGO   (Spain)

^b UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

COOPERATIVE EFFECTS; COOPERATIVITY; CROSS-COUPLINGS; DETRIMENTAL EFFECTS; DFT COMPUTATIONS; NEGISHI COUPLING; OXIDATIVE ADDITIONS; PD COMPLEX; REDUCTIVE ELIMINATION; TRANSMETALATION; VINYL BROMIDES;

BROMINE COMPOUNDS; PALLADIUM COMPOUNDS;

ZINC;

EID: 84858140462     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om300024p     Document Type: Article

References (105)

1. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., de Meijere, A., Eds.; Wiley: New York, 2002.
2. Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
3. Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127-2198
4. Fu, G. C. Acc. Chem. Res. 2008, 41, 1555-1564
5. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.; de Meijere, A., Eds.; Wiley: New York, 2002; Part III.
6. Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979-2017
7. Negishi, E.; Zheng, X.; Tan, Z.; Mingxing, Q.; Hu, Q.; Huang, Z. In Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 815-889.
8. Phapale, V. B.; Cárdenas, D. J. Chem. Soc. Rev. 2009, 38, 1598-1607
9. Negishi, E.; Wang, G. W.; Rao, H. H.; Xu, Z. Q. J. Org. Chem. 2010, 75, 3151-3182
10. Echavarren, A. M.; Cárdenas, D. J. In Metal-Catalyzed Cross-Coupling Reactions, 2 nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 1, pp 1-40.
11. Xue, L.; Lin, Z. Chem. Soc. Rev. 2010, 39, 1692-1705
12. Some differences have been established between the nickel- and palladium-catalyzed pathways. For example, in the alkyl-alkyl coupling under nickel catalysis the conventional order of events mentioned above is altered so that transmetalation takes place before oxidative addition and reductive elimination: Phapale, V. B.; Guisán-Ceinos, M.; Buñuel, E.; Cárdenas, D. J. Chem. Eur. J. 2009, 15, 12681-12688
13. Chass, G. A.; Kantchev, E. A. B.; Fang, D. C. Chem. Commun. 2010, 46, 2727-2729
14. See also ref 2d.
15. Casares, J. A.; Espinet, P.; Fuentes, B.; Salas, G. J. Am. Chem. Soc. 2007, 129, 3508-3509
16. Fuentes, B.; García-Melchor, M.; Lledós, A.; Maseras, F.; Casares, J. A.; Ujaque, G.; Espinet, P. Chem. Eur. J. 2010, 16, 8596-8599
17. García-Melchor, M.; Fuentes, B.; Lledós, A.; Casares, J. A.; Ujaque, G.; Espinet, P. J. Am. Chem. Soc. 2011, 133, 13519-13526
18. Liu, Q.; Lan, L.; Liu, L.; Li, G.; Wu, Y. D.; Lei, A. W. J. Am. Chem. Soc. 2009, 131, 10201-10210
19. Álvarez, R.; de Lera, A. R.; Aurrecoechea, J. M.; Durana, A. Organometallics 2007, 26, 2799-2802
20. Chass, G. A.; O'Brien, C. J.; Hadei, N.; Kantchev, E. A. B.; Mu, W. H.; Fang, D. C.; Hopkinson, A. G.; Csizmadia, I. G.; Organ, M. G. Chem. Eur. J. 2009, 15, 4281-4288
21. Insights into the role of added halides in the Negishi coupling using the NHC ligand on Pd have been reported: Achonduh, G. T.; Hadei, N.; Valente, C.; Avola, S.; O'Brien, C. J.; Organ, M. G. Chem. Commun. 2010, 46, 4109-4111
22. Musaev, D. G.; Liebeskind, L. S. Organometallics 2009, 28, 4639-4642
23. Ogoshi, S.; Ueta, M.; Arai, T.; Kurosawa, H. J. Am. Chem. Soc. 2005, 127, 12810-12811
24. Weng, Z. Q.; Teo, S.; Koh, L. L.; Hor, T. S. A. Chem. Commun. 2006, 1319-1321
25. Jones, C.; Rose, R. P.; Stasch, A. Dalton Trans. 2007, 2997-2999
26. Cadenbach, T.; Bollermann, T.; Gemel, C.; Fernández, I.; von Hopffgarten, M.; Frenking, G.; Fischer, R. A. Angew. Chem., Int. Ed. 2008, 47, 9150-9154
27. Kays, D. L.; Aldridge, S. Angew. Chem., Int. Ed. 2009, 48, 4109-4111
28. Wagler, J.; Hill, A. F.; Heine, T. Eur. J. Inorg. Chem. 2008, 4225-4229
29. Kim, M.; Taylor, T. J.; Gabbaï, F. P. J. Am. Chem. Soc. 2008, 130, 6332-6333
30. Gualco, P.; Lin, T.-P.; Sircoglou, M.; Mercy, M.; Ladeira, S.; Bouhadir, G.; Pérez, L. M.; Amgoune, A.; Maron, L.; Gabbaï, F. P.; Bourissou, D. Angew. Chem., Int. Ed. 2009, 48, 9892-9895
31. Moret, M.-E.; Serra, D.; Bach, A.; Chen, P. Angew. Chem., Int. Ed. 2010, 49, 2873-2877
32. For an example of a different fully bimetallic reaction pathway involving Co-Rh bonds, see: Yoshikai, N.; Yamanaka, M.; Ojima, I.; Morokuma, K.; Nakamura, E. Organometallics 2006, 25, 3867-3875
33. Shenglof, M.; Molander, G. A.; Blum, J. Synthesis 2006, 111-114
34. Tanaka, S. I.; Hoh, H.; Akahane, Y.; Tsutsuminai, S.; Komine, N.; Hirano, M.; Komiya, S. J. Organomet. Chem. 2007, 692, 26-35
35. Chaplin, A. B.; Weller, A. S. Angew. Chem., Int. Ed. 2010, 49, 581-584
36. For a recent review, see: Hirner, J. J.; Shi, Y.; Blum, S. A. Acc. Chem. Res. 2011, 44, 603-613
37. 2Zn: Hratchian, H. P.; Chowdhury, S. K.; Gutiérrez-Garcia, V. M.; Amarasinghe, K. K. D.; Heeg, M. J.; Schlegel, H. B.; Montgomery, J. Organometallics 2004, 23, 4636-4646
38. For calculations on a Pd-catalyzed reaction believed to proceed through intermediates with a Pd-Sn bond, see: Wang, M. Y.; Cheng, L.; Hong, B.; Wu, Z. J. J. Comput. Chem. 2009, 30, 1521-1531
39. Blake, A. J.; Shannon, J.; Stephens, J. C.; Woodward, S. Chem. Eur. J. 2007, 13, 2462-2472
40. Shannon, J.; Bernier, D.; Rawson, D.; Woodward, S. Chem. Commun. 2007, 3945-3947
41. Casado, A. L.; Casares, J. A.; Espinet, P. Inorg. Chem. 1998, 37, 4154-4156
42. Casado, A. L.; Espinet, P. Organometallics 1998, 17, 954-959
43. Goossen, L. J.; Koley, D.; Hermann, H. L.; Thiel, W. Organometallics 2005, 24, 2398-2410
44. Pérez-Temprano, M. H.; Gallego, A. M.; Casares, J. A.; Espinet, P. Organometallics 2011, 30, 611-617
45. Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704-4734
46. Nova, A.; Ujaque, G.; Maseras, F.; Lledós, A.; Espinet, P. J. Am. Chem. Soc. 2006, 128, 14571-14578
47. Álvarez, R.; Nieto Faza, O.; Silva López, C.; de Lera, A. R. Org. Lett. 2006, 8, 35-38
48. Braga, A. A. C.; Ujaque, G.; Maseras, F. Organometallics 2006, 25, 3647-3658
49. Álvarez, R.; Faza, O. N.; de Lera, A. R.; Cárdenas, D. J. Adv. Synth. Catal. 2007, 349, 887-906
50. Álvarez, R.; Pérez, M.; Nieto Faza, O.; de Lera, A. R. Organometallics 2008, 27, 3378-3389
51. Ahlquist, M.; Fristrup, P.; Tanner, D.; Norrby, P. O. Organometallics 2006, 25, 2066-2073
52. Barrios-Landeros, F.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 6944-6945
53. Ahlquist, M.; Norrby, P. O. Organometallics 2007, 26, 550-553
54. Lam, K. C.; Marder, T. B.; Lin, Z. Y. Organometallics 2007, 26, 758-760
55. Li, Z.; Fu, Y.; Guo, Q.-X.; Liu, L. Organometallics 2008, 27, 4043-4049
56. Barrios-Landeros, F.; Carrow, B. P.; Hartwig, J. F. J. Am. Chem. Soc. 2009, 131, 8141-8154
57. n (L = bulky phosphine; n = 1, 2) + PhX oxidative addition kinetics, see: McMullin, C. L.; Jover, J.; Harvey, J. N.; Fey, N. Dalton Trans. 2010, 39, 10833-10836
58. Besora, M.; Gourlaouen, C.; Yates, B.; Maseras, F. Dalton Trans. 2011, 40, 11089-11094
59. Galardon, E.; Ramdeehul, S.; Brown, J. M.; Cowley, A.; Hii, K. K.; Jutand, A. Angew. Chem., Int. Ed. 2002, 41, 1760-1763
60. Hills, I. B.; Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5749-5752
61. Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 12527-12530
62. Mitchell, E. A.; Jessop, P. G.; Baird, M. C. Organometallics 2009, 28, 6732-6738
63. Guerrero, A.; Hughes, D. L.; Bochmann, M. Organometallics 2006, 25, 1525-1527
64. MacIntosh, I. S.; Sherren, C. N.; Robertson, K. N.; Masuda, J. D.; Pye, C. C.; Clyburne, J. A. C. Organometallics 2010, 29, 2063-2068
65. Serra-Muns, A.; Jutand, A.; Moreno-Mañas, M.; Pleixats, R. Organometallics 2008, 27, 2421-2427
66. Amatore, C.; Carre, E.; Jutand, A.; M'Barki, M. A. Organometallics 1995, 14, 1818-1826
67. Kakino, R.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2001, 74, 371-376
68. Zapf, A.; Beller, M. Chem. Eur. J. 2001, 7, 2908-2915
69. Wegner, H. A.; Scott, L. T.; de Meijere, A. J. Org. Chem. 2003, 68, 883-887
70. Molander, G. A.; Fumagalli, T. J. Org. Chem. 2006, 71, 5743-5747
71. Endo, M.; Fugami, K.; Enokido, T.; Sano, H.; Kosugi, M. Adv. Synth. Catal. 2007, 349, 1025-1027
72. 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, J. M.; 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 A.1; Gaussian, Inc., Wallingford, CT, 2009.
73. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
74. Ziegler, T. Chem. Rev. 1991, 91, 651-667
75. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
76. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
77. Adamo, C.; Barone, V. J. Chem. Phys. 1998, 108, 664-675
78. Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157-167
79. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
80. Grimme, S. J. Comput. Chem. 2006, 27, 1787-1799
81. Onsager, L. J. Am. Chem. Soc. 1936, 58, 1486-1493
82. Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027-2094
83. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3094
84. Andrae, D.; Häussermann, U.; Dolg, M.; Stoll, H.; Preuss, H. Theor. Chim. Acta 1990, 77, 123-141
85. Bauernschmitt, R.; Ahlrichs, R. J. Chem. Phys. 1996, 22, 9047-9052
86. Peng, C.; Schlegel, H. B. Isr. J. Chem. 1993, 33, 449-454
87. Peng, C.; Ayala, H. B.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49-56
88. LaLonde, R. L.; Brenzovich, W. E., Jr.; Benítez, D.; Tkatchouk, E.; Kelley, K.; Goddard, W. A., III; Toste, F. D. Chem. Sci. 2010, 1, 226-233
89. González, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527
90. X-ray data for a complex with a Pd-Zn covalent bond have been recently reported: Fafard, C. M.; Chen, C. H.; Foxman, B. M.; Ozerov, O. V. Chem. Commun. 2007, 4465-4467
91. Ariafard, A.; Lin, Z. Y. Organometallics 2006, 25, 4030-4033
92. Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 9651-9653
93. Deprez, N. R.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 11234-11241
94. Powers, D. C.; Geibel, M. A. L.; Klein, J. E. M. N.; Ritter, T. J. Am. Chem. Soc. 2009, 131, 17050-17051
95. Powers, D. C.; Ritter, T. Nat. Chem. 2009, 1, 302-309
96. Markov, A. A.; Klyagina, A. P.; Dolin, S. P.; Akhmadullina, N. S.; Kozitsyna, N. Y.; Cherkashina, N. V.; Nefedov, S. E.; Vargaftik, M. N.; Moiseev, I. I. Russ. J. Inorg. Chem. 2009, 54, 885-892
97. See also ref 9.
98. For a recent example of Pd/Zn cooperativity in a multinuclear catalyst, see: Endo, K.; Tanaka, K.; Ogawa, M.; Shibata, T. Org. Lett. 2011, 13, 868-871
99. Fitton, P.; Johnson, M. P.; McKeon, J. E. Chem. Commun. (London) 1968, 6-7
100. 2 Negishi coupling using a monoligated phosphabarrelene Pd complex also found low activation energies for the transmetalation step: Ribagnac, P.; Blug, M.; Villa-Uribe, J.; Le Goff, X.-F.; Gosmini, C.; Mézailles, N. Chem. Eur. J. 2011, 17, 14389-14393
101. Ananikov, V. P.; Musaev, D. G.; Morokuma, K. Organometallics 2005, 24, 715-723
102. Ariafard, A.; Yates, B. F. J. Organomet. Chem. 2009, 694, 2075-2084
103. Pérez-Rodríguez, M.; Braga, A. A. C.; García- Melchor, M.; Pérez-Temprano, M. H.; Casares, J. A.; Ujaque, G.; de Lera, A. R.; Álvarez, R.; Maseras, F.; Espinet, P. J. Am. Chem. Soc. 2009, 131, 3650-3657
104. Pérez-Rodríguez, M.; Braga, A. A. C.; de Lera, A. R.; Maseras, F.; Álvarez, R.; Espinet, P. Organometallics 2010, 29, 4983-4991
105. Sajith, P. K.; Suresh, C. H. Inorg. Chem. 2011, 50, 8085-8093