Boryl anion attacks transition-metal chlorides to form boryl complexes: Syntheses, spectroscopic, and structural studies on group 11 borylmetal complexes

Angewandte Chemie - International Edition

Volumn 46, Issue 35, 2007, Pages 6710-6713

  Segawa, Yasutomo ^a   Yamashita, Makoto ^a   Nozaki, Kyoko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

B ligands; Boron; Boryl anion; Group 11 elements; Structure elucidation

Indexed keywords

CHLORINE COMPOUNDS; COMPLEXATION; NEGATIVE IONS; SPECTROSCOPIC ANALYSIS; SYNTHESIS (CHEMICAL); TRANSITION METALS;

B LIGANDS; BORYL ANIONS; BORYL LIGANDS; STRUCTURE ELUCIDATION;

BORON COMPOUNDS;

EID: 34548646273     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200702369     Document Type: Article

References (63)

1. a) G. J. Irvine, M. J. G. Lesley, T. B. Marder, N. C. Norman, C. R. Rice, E. G. Robins, W. R. Roper, G. R. Whittell, L. J. Wright, Chem. Rev. 1998, 98, 2685-2722;
2. b) H. Braunschweig, Angew. Chem. 1998, 110, 1882-1898;
3. Angew. Chem. Int. Ed. 1998, 37, 1786-1801;
4. c) H. Braunschweig, M. Colling, Coord. Chem. Rev. 2001, 223, 1-51;
5. d) H. Braunschweig, C. Kollann, D. Rais, Angew. Chem. 2006, 118, 5380-5400;
6. Angew. Chem. Int. Ed. 2006, 45, 5254-5274;
7. e) M. R. Smith III, Prog. Inorg. Chem. 1999, 48, 505-567;
8. f) S. Aldridge, D. L. Coombs, Coord. Chem. Rev. 2004, 248, 535-559.
9. a) D. Männig, H. Nöth, Angew. Chem. 1985, 97, 854-855;
10. Angew. Chem. Int. Ed. Engl. 1985, 24, 878-879;
11. b) T. Ishiyama, J. Takagi, K. Ishida, N. Miyaura, N. R. Anastasi, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 390-391.
12. a) K. M. Waltz, J. F. Hartwig, J. Am. Chem. Soc. 2000, 122, 11358-11369;
13. b) T. M. Boller, J. M. Murphy, M. Hapke, T. Ishiyama, N. Miyaura, J. F. Hartwig, J. Am. Chem. Soc. 2005, 127, 14263-14278;
14. c) S. A. Westcott, N. J. Taylor, T. B. Marder, R. T. Baker, N. J. Jones, J. C. Calabrese, J. Chem. Soc. Chem. Commun. 1991, 304-305;
15. d) R. T. Baker, J. C. Calabrese, S. A. Westcott, P. Nguyen, T. B. Marder, J. Am. Chem. Soc. 1993, 115, 4367-4368;
16. e) G. Lesley, P. Nguyen, N. J. Taylor, T. B. Marder, A. J. Scott, W. Clegg, N. C. Norman, Organometallics 1996, 15, 5137-5154.
17. The first example of a boryl complex synthesized by salt elimination: H. Nöth, G. Schmid, Angew. Chem. 1963, 75, 861-862;
18. Angew. Chem. Int. Ed. Engl. 1963, 2, 623;
19. the first structurally characterized boryl complex made by salt elimination: J. F. Hartwig, S. Huber, J. Am. Chem. Soc. 1993, 115, 4908-4909.
20. The first example of a boryl complex synthesized by oxidative addition: G. Schmid, H. Nöth, Z. Naturforsch. B 1965, 20, 1008-1008;
21. the first structurally characterized boryl complex made by oxidative addition: R. T. Baker, D. W. Ovenall, J. C. Calabrese, S. A. Westcott, N. J. Taylor, I. D. Williams, T. B. Marder, J. Am. Chem. Soc. 1990, 112, 9399-9400.
22. Y. Kawano, T. Yasue, M. Shimoi, J. Am. Chem. Soc. 1999, 121, 11744-11750.
23. a) K. Takahashi, T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2001, 625, 47-53;
24. b) H. Ito, C. Kawakami, M. Sawamura, J. Am. Chem. Soc. 2005, 127, 16034-16035.
25. D. S. Laitar, P. Mueller, J. P. Sadighi, J. Am. Chem. Soc. 2005, 127, 17196-17197.
26. Y. Segawa, M. Yamashita, K. Nozaki, Science 2006, 314, 113-115.
27. M. Yamashita, Y. Suzuki, Y. Segawa, K. Nozaki, J. Am. Chem. Soc. 2007, DOI: 10.1021/ja073037t.
28. a) W. A. Herrmann, C. Köcher, Angew. Chem. 1997, 109, 2256-2282;
29. Angew. Chem. Int. Ed. Engl. 1997, 36, 2162-2187;
30. b) W. A. Herrmann, Angew. Chem. 2002, 114, 1342-1363;
31. Angew. Chem. Int. Ed. 2002, 41, 1290-1309.
32. a) R. Dorta, E. D. Stevens, N. M. Scott, C. Costabile, L. Cavallo, C. D. Hoff, S. P. Nolan, J. Am. Chem. Soc. 2005, 127, 2485-2495;
33. b) A. C. Hillier, W. J. Sommer, B. S. Yong, J. L. Petersen, L. Cavallo, S. P. Nolan, Organometallics 2003, 22, 4322-4326.
34. a) M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 2247-2250;
35. b) M. S. Sanford, M. Ulman, R. H. Grubbs, J. Am. Chem. Soc. 2001, 123, 749-750;
36. c) M. S. Sanford, J. A. Love, R. H. Grubbs, J. Am. Chem. Soc. 2001, 123, 6543-6554.
37. Recently, Braunschweig indicated the possibility of a significant development in the area of metal boryl complexes using boryllithium, see: H. Braunschweig, Angew. Chem. 2007, 119, 1990-1992;
38. Angew. Chem. Int. Ed. 2007, 46, 1946-1948;
39. a related synthesis of gallyl complexes using gallyl anions was reported, see: S. P. Green, C. Jones, D. P. Mills, A. Stasch, Organometallics 2007, 26, 3424-3430.
40. a) L. Weber, Coord. Chem. Rev. 2001, 215, 39-77;
41. b) L. Weber, Coord. Chem. Rev. 2007, DOI: 10.1016/j.ccr.2007.02.014.
42. max = 55°. The structures were solved by direct methods with SIR-97 (A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115-119)
43. 2 SHELXL-97 (G. M. Sheldrick, SHELXL-97, Program for the Refinement of Crystal Structures; University of Göttingen, Göttingen, Germany, 1997) The intensities were corrected for Lorentz and polarization effects. The non-hydrogen atoms were refined anisotropically. Hydrogen atoms were refined isotropically in the difference Fourier maps or placed using AFIX instructions. CCDC-648270 (3b), CCDC-648271 (4a), CCDC-648272 (4b), CCDC-648273 (5a), CCDC-648274 (5b), CCDC-648275 (6a), CCDC-648276 (6b), CCDC-648277 (7a), and CCDC-648278 (7b) contain 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.ulc/data_request/cif.
44. The Cambridge Crystallographic Database showed 20 structures containing a B-Ag bond. In all of these complexes, B-Ag bonds can be considered as three-center-two-electron bonds with bridging hydrogen atoms. The shortest example of a B-Ag bond is 2.352(4) Å; see: H. M. Colquhoun, T. J. Greenhough, M. G. H. Wallbridge, J. Chem. Soc. Chem. Commun. 1980, 192-194.
45. The Cambridge Crystallographic Database showed 61 structures containing B-Au bond. In all of these complexes, the B-Au bonds can be considered as multicenter-multielectron bonds. The shortest example of a B-Au bond is 2.15(1) Å; see: A. J. C. Jeffery, P. A. Jelliss, F. G. A. Stone, Organometallics 1994, 13, 2651-2661.
46. a) C. Y. Dai, G. Stringer, T. B. Marder, A. J. Scott, W. Clegg, N. C. Norman, Inorg. Chem. 1997, 36, 272-273;
47. b) G. Sivignon, P. Fleurat-Lessard, J. M. Onno, F. Volatron, Inorg. Chem. 2002, 41, 6656-6661;
48. c) W. H. Lam, K. C. Lam, Z. Y. Lin, S. Shimada, R. N. Perutz, T. B. Marder, Dalton Trans. 2004, 1556-1562;
49. d) H. Braunschweig, K. Radacki, D. Rais, F. Seeler, Organometallics 2004, 23, 5545-5549;
50. e) H. Braunschweig, K. Radacki, D. Rais, D. Scheschkewitz, Angew. Chem. 2005, 117, 5796-5799;
51. Angew. Chem. Int. Ed. 2005, 44, 5651-5654.
52. J. Zhu, Z. Y. Lin, T. B. Marder, Inorg. Chem. 2005, 44, 9384-9390.
53. T. Ramnial, C. D. Abernethy, M. D. Spicer, I. D. McKenzie, I. D. Gay, J. A. C. Clyburne, Inorg. Chem. 2003, 42, 1391-1393.
54. a) S. J. Archibald, N. W. Alcock, D. H. Busch, D. R. Whitcomb, Inorg. Chem. 1999, 38, 5571-5578;
55. b) A. F. M. J. van der Ploeg, G. van Koten, C. Brevard, Inorg. Chem. 1982, 21, 2878-2881.
56. S. Okamoto, S. Tominaga, N. Saino, K. Kase, K. Shimoda, J. Organomet. Chem. 2005, 690, 6001-6007.
57. P. de Fremont, N. M. Scott, E. D. Stevens, S. P. Nolan, Organometallics 2005, 24, 2411-2418.
58. a) N. C. Baenziger, W. E. Bennett, D. M. Soboroff, Acta Crystallogr. Sect. B 1976, 32, 962-963;
59. b) P. D. Gavens, J. J. Guy, M. J. Mays, G. M. Sheldrick, Acta Crystallogr. Sect. B 1977, 33, 137-139;
60. c) X. Hong, K. K. Cheung, C. X. Guo, C. M. Che, J. Chem. Soc. Dalton Trans. 1994, 1867-1871.
61. J. P. Desclaux, P. Pyykko, Chem. Phys Lett. 1976, 39, 300-303.
62. F. Scherbaum, A. Grohmann, B. Huber, C. Krüger, H. Schmidbaur, Angew. Chem. 1988, 100, 1602-1604;
63. Angew. Chem. Int. Ed. Engl. 1988, 27, 1544-1546.