Nickel complexes of a pincer amidobis(amine) ligand: Synthesis, structure, and activity in stoichiometric and catalytic C-C bond-forming reactions of alkyl halides

Chemistry - A European Journal

Volumn 15, Issue 15, 2009, Pages 3889-3899

  Vechorkin, Oleg ^a   Csok, Zsolt ^a   Scopelliti, Rosario ^a   Hu, Xile ^a  

^a EPFL   (Switzerland)

Author keywords

C C coupling; Coordination modes; Cross coupling; Nickel; Pincer ligands

Indexed keywords

ALKYL HALIDES; C-C BOND FORMATIONS; C-C BOND FORMING REACTIONS; C-C COUPLING; CATIONIC COMPLEXES; CHLORIDE ABSTRACTIONS; COORDINATION CHEMISTRIES; COORDINATION MODES; CROSS-COUPLING; CROSS-COUPLING REACTIONS; ELECTROCHEMICAL MEASUREMENTS; ELECTRON-DONATING PROPERTIES; GOOD YIELDS; GRIGNARD REAGENTS; LEWIS ACIDITIES; LIGAND COORDINATES; MONOHALIDES; NICKEL COMPLEXES; NMR CHEMICAL SHIFTS; PINCER LIGANDS; PRECATALYST; RADICAL PATHWAYS; SALT METATHESIS; SOLID-STATE STRUCTURES; SQUARE-PLANAR COORDINATIONS;

ALKYLATION; AMINES; BROMINE COMPOUNDS; CHELATION; CHEMICAL BONDS; CHLORINE COMPOUNDS; COMPLEXATION; DYES; ELECTROCHEMICAL PROPERTIES; FORMING; NICKEL; NICKEL ALLOYS; NICKEL COMPOUNDS; ORGANIC COMPOUNDS; PHOSPHORUS COMPOUNDS;

LIGANDS;

EID: 63849273175     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802059     Document Type: Article

References (74)

1. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed. (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004.
2. J. P. Corbet, G. Mignani, Chem. Rev. 2006,106,2651- 2710.
3. a) D. J. Cárdenas, Angew. Chem. 2003, 115, 398-401;
4. Angew. Chem. Int. Ed. 2003, 42, 384-387;
5. b) A. C. Frisch, M. Beller, Angew. Chem. 2005,117, 680-695;
6. Angew. Chem. Int. Ed. 2005, 44, 674-688.
7. M. R. Netherton, G. C. Fu, Adv. Synth. Catal. 2004, 346, 1525-1532.
8. A. Ariafard, Z. Y. Lin, Organometallics 2006, 25, 4030-4033.
9. a) A. E. Jensen, P. Knöchel, J. Org. Chem. 2002, 67, 79-85;
10. b) R. Giovannini, T. Studemann, G. Dussin, P. Knöchel, Angew. Chem. 1998, 110, 2512-2515;
11. Angew. Chem. Int. Ed. 1998, 37, 2387-2390.
12. J. Terao, H. Watanabe, A. Ikumi, H. Kuniyasu, N. Kambe, J. Am. Chem. Soc. 2002, 124, 4222-4223.
13. J. Terao, N. Kambe, Bull. Chem. Soc. Jpn. 2006, 79, 663-672.
14. a) M. R. Netherton, C. Y. Dai, K. Neuschutz, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 10099-10100;
15. b) J. H. Kirchhoff, C. Y. Dai, G. C. Fu, Angew. Chem. 2002, 114, 2025-2027;
16. Angew. Chem. Int. Ed. 2002, 41, 1945-1947;
17. c) J. R. Zhou, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 12527-12530;
18. d) B. Saito, G. C. Fu, J. Am. Chem. Soc. 2007, 129, 9602-9603.
19. a) J. R. Zhou, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 14726-14727;
20. b) N. A. Strotman, S. Sommer, G. C. Fu, Angew. Chem. 2007, 119, 3626-3628;
21. Angew. Chem. Int. Ed. 2007, 46, 3556-3558.
22. C. Fischer, G. C. Fu, J. Am. Chem. Soc. 2005, 127, 4594-4595.
23. G. D. Jones, J. L. Martin, C. McFarland, O. R. Allen, R. E. Hall, A. D. Haley, R. J. Brandon, T. Konovalova, P. J. Desrochers, P. Pulay, D. A. Vicie, J. Am. Chem. Soc. 2006, 128, 13175-13183.
24. T. J. Anderson, G. D. Jones, D. A. Vicie, J. Am. Chem. Soc. 2004, 126, 8100-8101
25. V. B. Phapale, E. Bunuel, M. Garcia-Iglesias, D. J. Cárdenas, Angew. Chem. 2007, 119, 8946-8951;
26. Angew. Chem. Int. Ed. 2007, 46, 8790-8795.
27. J. G. Donkervoort, J. L. Vicario, J. Jastrzebski, R. A. Gossage, G. Cahiez, G. van Koten, J. Organomet. Chem. 1998, 558, 61-69.
28. G. Cahiez, C. Chaboche, M. Jezequel, Tetrahedron 2000, 56, 2733-2737.
29. M. Nakamura, K. Matsuo, S. Ito, B. Nakamura, J. Am. Chem. Soc. 2004, 126, 3686-3687.
30. R. Martin, A. Fürstner, Angew. Chem. 2004, 116, 4045-4047;
31. Angew. Chem. Int. Ed. 2004, 43, 3955-3957.
32. X. F. Lin, D. L. Phillips, J. Org. Chem. 2008, 73, 3680-3688.
33. Z. Csok, O. Vechorkin, S. B. Harkins, R. Scopelliti, X. L. Hu, J. Am. Chem. Soc. 2008, 130, 8156-8157.
34. M. D. Fryzuk, P. A. Macneil, S. J. Rettig, A. S. Secco, J. Trotter, Organometallics 1982, 1, 918-930.
35. a) M. D. Fryzuk, P. A. Macneil, Organometallics 1983, 2, 682-684;
36. b) M. E. van der Boom, D. Milstein, Chem. Rev. 2003, 103, 1759-1792.
37. M. Albrecht, G. van Koten, Angew. Chem. 2001, 113, 3866-3898;
38. Angew. Chem. Int. Ed. 2001, 40, 3750-3781,
39. a) C. Gunanathan, Y. Ben-David, D. Milstein, Science 2007, 317, 790-792;
40. b) M. D. Fryzuk, V. Hoffman, J. E. Kickham, S. J. Rettig, S. Gambarotta, Inorg. Chem. 1997, 36, 3480-3484;
41. c) A. Walstrom, M. Pink, X. F. Yang, J. Tomaszewski, M. H. Baik, K. G. Caulton, J. Am. Chem. Soc. 2005, 127, 5330-5331;
42. d) J. H. Lee, M. Pink, K. G. Caulton, Organometallics 2006, 25, 802-804;
43. e) S. Gatard, R. Celenligil-Cetin, C. Y. Guo, B. M. Foxman, O. V. Ozerov, J. Am. Chem. Soc. 2006, 128, 2808-2809;
44. f) L. Fan, S. Parkin, O. V. Ozerov, J. Am. Chem. Soc. 2005, 127, 16772-16773;
45. g) C. M. Fafard, D. Adhikari, B. M. Foxman, D. J. Mindiola, O. V. Ozerov, J. Am. Chem. Soc. 2007, 129, 10318-10319;
46. h) B. C. Bailey, J. C. Huffman, D. J. Mindio la,J. Am. Chem. Soc. 2007,129, 5302-5303;
47. i) L. C. Liang, J. M. Lin, C. H. Hung, Organometallics 2003, 22, 3007-3009;
48. j) L. C. Liang, P. S. Chien, Y. L. Huang, J. Am. Chem. Soc. 2006, 128, 15562-15563;
49. k) L.C. Liang, Coord. Chem. Rev. 2006, 250, 1152-1177;
50. l) D. Benito-Garagorri, K. Kirchner, Acc. Chem. Res. 2008, 41, 201-213;
51. m) V. Pandaras, D. Zargarian, Chem. Commun. 2007, 978-980;
52. n) B. M. Cochran, F. E. Michael, J. Am. Chem. Soc. 2008, 130, 2786-2792.
53. L. C. Liang, P. S. Chien, J. M. Lin, M. H. Huang, Y. L. Huang, J. H. Liao, Organometallics 2006, 25, 1399-1411
54. L. Fan, O. V. Ozerov, Chem. Commun. 2005, 4450-4452.
55. a) S. Gosiewska, S. M. Herreras, M. Lutz, A. L. Spek, R. W. A. Havenith, G. P. M., van Klink, G. van Koten, R. J. M. K. Gebbink, Organometallics 2008, 27, 2549-2559;
56. b) M. Gagliardo, D. J. M. Snelders, P. A. Chase, R. J. M. K. Gebbink, G. P. M. van Klink, G. van Koten, Angew. Chem, 2007, 119, 8710-8726;
57. Angew. Chem. Int. Ed. 2007, 46, 8558-8573;
58. c) J.C. Peters, S.B. Harkins, S.D. Brown, M.W. Day, Inorg. Chem. 2001, 40, 5083-5091;
59. d) S. B. Harkins, J. C. Peters, Organometallics 2002, 21, 1753-1755;
60. e) Z. X. Wang, L. Wang, Chem. Commun. 2007, 2423-2425;
61. f) H. Nishiyama, Chem. Soc. Rev. 2007, 56, 1133-1141
62. J. S. Fossey, C. J. Richards, Organometallics 2004, 23, 367-373.
63. A. Bugarin, B. T. Connell, Organometallics 2008, 27, 4357-4369.
64. V. Pandarus, D. Zargarian, Organometallics 2007, 26, 4321-4334.
65. R. H. Crabtree, The Organometallic Chemistry of Transition Metals, 4th ed., Wiley, New York, 2005.
66. According to the Cambridge Structural Database, there are more than 100 Ni acetate complexes in which acetate is coordinated similarly; CSD version 5.29 updates (January 2008).
67. A. Castonguay, F. Charbonneau, A. L. Beauchamp, D. Zargarian, Acta Crystallogr. Sect. E 2005, 61, m2240-m2241
68. A. V. Joshi, M. Baidossi, N. Taha, S. Mukhopadhyay, Y. Sasson, Synth. Commun. 2005,35, 2715-2722.
69. a) S. de Castro, R. Chicharro, V. J. Aran, J. Chem. Soc. Perkin Trans. 1 2002, 790-802;
70. b) D. P. Kelly, S.A. Bateman, R.J. Hook, R. F. Martin, M. E. Reum, M. Rose, A. R. D. Whittaker, Aust. J. Chem. 1994, 47, 1751-1769;
71. c) J. T. Gupton, J. P. Idoux, G. Baker, C. Colon, A. D. Crews, C. D. Jurss, R. C. Rampi, J. Org. Chem. 1983, 48, 2933-2936.
72. CrysAlis PRO, Oxford Diffraction Ltd., Abingdon, Oxfordshire, OX14 1RL, UK, 2008.
73. R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-38.
74. G. M. Sheldrick, SHELXTL, University of Gottingen, Göttingen, Germany, 1997.