Extending the chain: Synthetic, structural, and reaction chemistry of a BN allenylidene analogue

Angewandte Chemie - International Edition

Volumn 50, Issue 38, 2011, Pages 8908-8911

  Niemeyer, Jochen ^a   Addy, David A ^a   Riddlestone, Ian ^a   Kelly, Michael ^a   Thompson, Amber L ^a   Vidovic, Dragoslav ^a   Aldridge, Simon ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

allenylidenes; boron ligands; borylene; halide abstraction; iron

Indexed keywords

ALLENYLIDENES; BORON LIGANDS; BORYLENES; DFT CALCULATION; HALIDE ABSTRACTION; REACTION CHEMISTRY;

ABSTRACTING; BORON COMPOUNDS;

BORON;

EID: 80052584425     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201103757     Document Type: Article

References (82)

1. H. Braunschweig, R. D. Dewhurst, A. Schneider, Chem. Rev. 2010, 110, 3924-3957.
2. G. J. Irvine, M. J. G. Lesley, T. B. Marder, N. C. Norman, C. R. Rice, E. G. Robbins, W. R. Roper, G. R. Whittell, L. J. Wright, Chem. Rev. 1998, 98, 2685-2722
3. D. L. Kays, S. Aldridge, Struct. Bonding 2008, 130, 29-122.
4. T. B. Marder, N. C. Morman, Top. Catal. 1998, 5, 63-73
5. T. Ishiyama, N. Miyaura, Chem. Rec. 2004, 3, 271-280
6. N. Miyaura, Bull. Chem. Soc. Jpn. 2008, 81, 1535-1553.
7. For a recent review see, for example:, C. M. Crudden, D. Edwards, Eur. J. Org. Chem. 2003, 4695-4712.
8. T. Ishiyama, N. Miyaura, in Handbook of C-H Transformations, Vol. 1 (Ed.:, G. Dyker,), Wiley-VCH, Weinheim, 2005, pp. 126-131
9. J. F. Hartwig, J. D. Lawrence, in Handbook of C-H Transformations, Vol. 2 (Ed.:, G. Dyker,), Wiley-VCH, Weinheim, 2005, pp. 605-616
10. F. Shi, M. R. Smith, R. E. Maleczka, Org. Lett. 2006, 8, 1411-1414
11. T. A. Boebel, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 7534-7535
12. P. Harrisson, J. Morris, T. B. Marder, P. G. Steel, Org. Lett. 2009, 11, 3586-3589.
13. A. Staubitz, M. E. Sloan, A. P. M. Robertson, A. Friedrich, S. Schneider, P. J. Gates, J. M. Schmedt auf der Günne, I. Manners, J. Am. Chem. Soc. 2010, 132, 13332-13345.
14. G. Alcaraz, L. Vendier, E. Clot, S. Sabo-Etienne, Angew. Chem. 2010, 122, 930-932
15. Angew. Chem. Int. Ed. 2010, 49, 918-920
16. C. Y. Tang, A. L. Thompson, S. Aldridge, Angew. Chem. 2010, 122, 933-937
17. Angew. Chem. Int. Ed. 2010, 49, 921-925
18. Angew. Chem. 2010, 122, 933-937
19. C. Y. Tang, A. L. Thompson, S. Aldridge, J. Am. Chem. Soc. 2010, 132, 10578-10591
20. G. Alcaraz, A. B. Chaplin, C. J. Stevens, E. Clot, L. Vendier, A. S. Weller, S. Sabo-Etienne, Organometallics 2010, 29, 5591-5595
21. C. J. Stevens, R. Dallanegra, A. B. Chaplin, A. S. Weller, S. A. Macgregor, B. Ward, D. McKay, G. Alcaraz, S. Sabo-Etienne, Chem. Eur. J. 2011, 17, 3011-3020
22. D. Vidovic, D. A. Addy, T. Krämer, J. McGrady, S. Aldridge, J. Am. Chem. Soc. 2011, 133, 8494-8497
23. M. O'Neill, D. A. Addy, I. Riddlestone, N. Phillips, M. Kelly, S. Aldridge, J. Am. Chem. Soc. 2011, 133, 11500-11503.
24. Y. Segawa, M. Yamashita, K. Nozaki, Science 2006, 314, 113-115
25. Y. Segawa, Y. Suzuki, M. Yamashita, K. Nozaki, J. Am. Chem. Soc. 2008, 130, 16069-16079.
26. D. Bourissou, O. Guerret, F. P. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39-92
27. S. Diez-Gonzalez, N. Marion, S. P. Nolan, Chem. Rev. 2009, 109, 3612-3676.
28. D. Vidovic, S. Aldridge, Angew. Chem. 2009, 121, 3723-3726
29. Angew. Chem. Int. Ed. 2009, 48, 3669-3672
30. Angew. Chem. 2009, 121, 3723-3726
31. X. Wang, B. O. Roos, L. Andrews, Angew. Chem. 2010, 122, 161-164
32. Angew. Chem. Int. Ed. 2010, 49, 157-160
33. Angew. Chem. 2010, 122, 161-166
34. H. Braunschweig, K. Radacki, A. Schneider, Science 2010, 328, 345-347
35. D. Vidovic, S. Aldridge, Chem. Sci. 2011, 2, 601-608. For related derivatives of heavier Group 13 monohalides, see
36. N. D. Coombs, W. Clegg, D. J. Willock, S. Aldridge, J. Am. Chem. Soc. 2008, 130, 5449-5451
37. N. D. Coombs, D. Vidovic, J. K. Day, A. L. Thompson, A. Stasch, W. Clegg, L. Russo, L. Male, M. B. Hursthouse, D. J. Willock, S. Aldridge, J. Am. Chem. Soc. 2008, 130, 16111-16124.
38. A. J. Ashe, Organometallics 2009, 28, 4236-4248.
39. For a recent article highlighting analogies between the isolectronic BN and CC units in materials science, see:, Z. Liu, T. B. Marder, Angew. Chem. 2008, 120, 248-250
40. Angew. Chem. Int. Ed. 2008, 47, 242-244
41. Angew. Chem. 2008, 120, 248-250.
42. H. Braunschweig, Adv. Organomet. Chem. 2004, 51, 163-192
43. S. Aldridge, D. L. Coombs, Coord. Chem. Rev. 2004, 248, 535-559
44. H. Braunschweig, D. Rais, Heteroat. Chem. 2005, 16, 566-571
45. H. Braunschweig, C. Kollann, D. Rais, Angew. Chem. 2006, 118, 5380-5400
46. Angew. Chem. Int. Ed. 2006, 45, 5254-5274
47. Angew. Chem. 2006, 118, 5380-5400
48. S. Aldridge, D. L. Kays, Main Group Chem. 2006, 5, 223-249
49. H. Braunschweig, C. Kollann, F. Seeler, Struct. Bonding 2008, 130, 1-27
50. D. Vidovic, G. A. Pierce, S. Aldridge, Chem. Commun. 2009, 1157-1171.
51. L. Apostolico, H. Braunschweig, A. G. Crawford, T. Herbst, D. Rais, Chem. Commun. 2008, 497-498
52. H. Braunschweig, T. Herbst, D. Rais, S. Ghosh, T. Kupfer, K. Radacki, A. G. Crawford, R. M. Ward, T. B. Marder, I. Fernández, G. Frenking, J. Am. Chem. Soc. 2009, 131, 8989-8999.
53. See, for example:, M. Akita, T. Koike, Dalton Trans. 2008, 3523-3530.
54. M. I. Bruce, Chem. Rev. 1998, 98, 2797-2858
55. C. Bruneau, P. Dixneuf, Angew. Chem. 2006, 118, 2232-2260
56. Angew. Chem. Int. Ed. 2006, 45, 2176-2203
57. Angew. Chem. 2006, 118, 2232-2260
58. Metal Vinylidenes and Allenylidenes in Catalysis (Eds.:, C. Bruneau, P. Dixneuf,), Wiley-VCH, Weinheim, 2008
59. V. Cadierno, J. Gimeno, Chem. Rev. 2009, 109, 3512-3560.
60. C. Cadierno, M. P. Gamasa, J. Gimeno, E. Lastra, J. Organomet. Chem. 1994, 474, C 27 -C 29
61. V. Cadierno, M. P. Gamasa, J. Gimeno, M. González-Cueva, E. Lastra, J. Borge, S. García-Granda, E. Pérez-Carreno, Organometallics 1996, 15, 2137-2147
62. M. A. Esteruelas, A. V. Gõmez, F. J. Lahoz, A. M. López, E. Onate, L. A. Oro, Organometallics 1996, 15, 3423-3435
63. M. P. Gamasa, J. Gimeno, C. González-Bernardo, J. Borge, S. García-Granda, Organometallics 1997, 16, 2483-2485
64. V. Cadierno, M. P. Gamasa, J. Gimeno, M. C. López-González, J. Borge, S. García-Granda, Organometallics 1997, 16, 4453-4463
65. M. A. Esteruelas, A. V. Gõmez, A. M. López, J. Modrego, E. Onate, Organometallics 1997, 16, 5826-5835.
66. S. Aldridge, R. J. Calder, R. E. Baghurst, M. E. Light, M. B. Hursthouse, J. Organomet. Chem. 2002, 649, 9-14
67. H. Braunschweig, K. Radacki, F. Seeler, G. R. Whittell, Organometallics 2004, 23, 4178-4180.
68. D. L. Coombs, S. Aldridge, C. Jones, D. J. Willock, J. Am. Chem. Soc. 2003, 125, 6356-6357
69. D. L. Coombs, S. Aldridge, A. Rossin, C. Jones, D. J. Willock, Organometallics 2004, 23, 2911-2926.
70. R. Anulewicz-Ostrowska, T. Klis, D. Krajewski, B. Lewandowski, J. Serwatowski, Tetrahedron Lett. 2003, 44, 7329-7331
71. A. B. Chaplin, A. S. Weller, Eur. J. Inorg. Chem. 2010, 5124-5128.
72. S. Aldridge, C. Jones, T. Gans-Eichler, A. Stasch, D. L. Kays, N. D. Coombs, D. J. Willock, Angew. Chem. 2006, 118, 6264-6268
73. Angew. Chem. Int. Ed. 2006, 45, 6118-6122
74. Angew. Chem. 2006, 118, 6264-6268.
75. G. A. Pierce, D. Vidovic, D. L. Kays, N. D. Coombs, A. L. Thompson, E. D. Jemmis, S. De, S. Aldridge, Organometallics 2009, 28, 2947-2960
76. S. De, G. A. Pierce, D. Vidovic, D. L. Kays, N. D. Coombs, E. D. Jemmis, S. Aldridge, Organometallics 2009, 28, 2961-2975.
77. G. Argouarch, P. Thominot, F. Paul, L. Toupet, C. Lapinte, C. R. Chim. 2003, 6, 209-222.
78. B. E. R. Schilling, R. Hoffmann, D. L. Lichtenberger, J. Am. Chem. Soc. 1979, 101, 585-591.
79. H. Braunschweig, T. Kupfer, K. Radacki, A. Schneider, F. Seeler, K. Uttinger, H. Wu, J. Am. Chem. Soc. 2008, 130, 7974-7983.
80. For a comparative quantum chemical analysis of cationic vinylidene/aminoborylene complexes see:, S. Aldridge, A. Rossin, D. L. Coombs, D. J. Willock, Dalton Trans. 2004, 2649-2654.
81. M. I. Bruce, P. Low, E. R. T. Tiekink, J. Organomet. Chem. 1999, 572, 3-10
82. V. Cadierno, S. Conejero, M. P. Gamasa, J. Gimeno, J. Chem. Soc. Dalton Trans. 2000, 451-457.