Transition-metal-free diboration reaction by activation of diboron compounds with simple lewis bases

Angewandte Chemie - International Edition

Volumn 50, Issue 31, 2011, Pages 7158-7161

  Bonet, Amadeu ^a   Pubill Ulldemolins, Cristina ^a,b   Bo, Carles ^b   Gulyás, Henrik ^a   Fernández, Elena ^a  

^a UNIVERSITAT ROVIRA I VIRGILI   (Spain)

^b INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

Author keywords

boron; density functional calculations; Lewis bases; organocatalysis

Indexed keywords

ANTIBONDING; COMPUTATIONAL STUDIES; DENSITY-FUNCTIONAL CALCULATIONS; DIBORATION; ELECTROPHILES; LEWIS BASE; LEWIS BASIS; ORGANOCATALYSIS;

BORON COMPOUNDS; OLEFINS; REACTION KINETICS; TRANSITION METALS;

BORON;

EID: 79960631995     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201101941     Document Type: Article

References (54)

1. Y. Segawa, M. Yamashita, K. Nozaki, Science 2006, 314, 113
2. T. B. Marder, Science 2006, 314, 69
3. H. Braunschweig, Angew. Chem. 2007, 119, 1990
4. Angew. Chem. Int. Ed. 2007, 46, 1946; see related papers
5. L. Dang, Z. Lin, T. B. Marder, Chem. Commun. 2009, 3987
6. M. Yamashita, Angew. Chem. 2010, 122, 2524
7. Angew. Chem. Int. Ed. 2010, 49, 2474.
8. K. Lee, A. R. Zhugralin, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 7253.
9. A. Bonet, H. Gulyás, E. Fernández, Angew. Chem. 2010, 122, 5256
10. Angew. Chem. Int. Ed. 2010, 49, 5130.
11. T. Ishiyama, N. Matsuda, N. Miyaura, A. Suzuki, J. Am. Chem. Soc. 1993, 115, 11018
12. T. Ishiyama, N. Matsuda, M. Murata, F. Ozawa, A. Suzuki, N. Miyaura, Organometallics 1996, 15, 713
13. T. Ishiyama, M. Yamamoto, N. Miyaura, Chem. Commun. 1997, 689
14. T. Ishiyama, N. Miyaura, Chem. Rec. 2004, 3, 271.
15. C. N. Iverson, M. R. Smith III, J. Am. Chem. Soc. 1995, 117, 4403
16. C. N. Iverson, M. R. Smith III, Organometallics 1997, 16, 2757
17. V. M. Dembitsky, H. Abu Ali, M. Srebnik, Appl. Organomet. Chem. 2003, 17, 327.
18. P. Nguyen, G. Lesley, N. J. Taylor, T. B. Marder, N. L. Pickett, W. Clegg, M. R. J. Elsegood, N. C. Norman, Inorg. Chem. 1994, 33, 4623-4624
19. R. T. Baker, P. Nguyen, T. B. Marder, S. A. Westcott, Angew. Chem. 1995, 107, 1451
20. Angew. Chem. Int. Ed. Engl. 1995, 34, 1336
21. T. B. Marder, N. C. Norman, Top. Catal. 1998, 5, 63
22. C. Dai, E. G. Robins, A. J. Scott, W. Clegg, D. S. Yufit, J. A. K. Howard, T. B. Marder, Chem. Commun. 1998, 1983
23. R. Ll. Thomas, F. E. S. Souza, T. B. Marder, J. Chem. Soc. Dalton Trans. 2001, 1650.
24. H. E. Burks, J. P. Morken, Chem. Commun. 2007, 4717.
25. J. B. Morgan, S. P. Miller, J. P. Morken, J. Am. Chem. Soc. 2003, 125, 8702
26. S. Trudeau, J. B. Morgan, M. Shrestha, J. P. Morken, J. Org. Chem. 2005, 70, 9538
27. J. Ramírez, A. M. Segarra, E. Fernández, Tetrahedron: Asymmetry 2005, 16, 1289
28. H. E. Burks, J. P. Morken, Chem. Commun. 2007, 4717
29. L. T. Kliman, S. N. Mlynarski, J. P. Morken, J. Am. Chem. Soc. 2009, 131, 13210
30. H. E. Burks, L. T. Kliman, J. P. Morken, J. Am. Chem. Soc. 2009, 131, 9134.
31. H. C. Brown, Boranes in Organic Chemistry, Cornell University Press, Ithaca, 1972.
32. G. M. L. Cragg, Organoboranes in Organic Synthesis, Dekker, New York, 1973.
33. H. C. Brown, Organic Synthesis via Boranes, Wiley-Interscience, New York, 1975.
34. T. Onak, in Organoborane Chemistry, Academic Press, New York, 1975.
35. A. Pelter, K. Smith, H. C. Brown, Borane Reagents, Academic Press, New York, 1988.
36. D. S. Matteson, Stereodirected Synthesis with Organoboranes, Springer, Berlin, 1995
37. D. G. Hall, Preparation and Applications in Organic Synthesis and Medicine, Wiley-VCH, Weinheim, 2005.
38. F. Yu, Ch-H. Cheng, J. Am. Chem. Soc. 2001, 123, 761.
39. N. F. Pelz, A. R. Woodward, H. E. Burks, J. D. Sieber, J. P. Morken, J. Am. Chem. Soc. 2004, 126, 16328.
40. A. R. Woodward, H. E. Burks, L. M. Chan, J. P. Morken, Org. Lett. 2005, 7, 5505.
41. P. Nguyen, C. Dai, N. J. Taylor, W. P. Power, T. B. Marder, N. L. Pickett, N. C. Normann, Inorg. Chem. 1995, 34, 4290.
42. W. Clegg, C. Dai, F. J. Lawlor, T. B. Marder, P. Nguyen, N. C. Norman, N. L. Pickett, W. P. Power, A. J. Scott, J. Chem. Soc. Dalton Trans. 1997, 839.
43. C. Dai, S. M. Johnson, F. J. Lawlor, P. Lightfoot, T. B. Marder, N. C. Norman, A. G. Orpen, N. L. Pickett, M. J. Quayle, C. R. Rice, Polyhedron 1998, 17, 4139.
44. M. Gao, S. B. Thorpe, W. L. Santos, Org. Lett. 2009, 11, 3478.
45. S. B. Thorpe, X. Guo, W. L. Santos, Chem. Commun. 2011, 47, 424.
46. K. Takahashi, T. Isiyama, N. Miyaura, J. Organomet. Chem. 2001, 625, 47
47. H. Zhao, L. Dang, T. B. Marder, Z. Lin, J. Am. Chem. Soc. 2008, 130, 5586
48. B. L. Tran, D. Adhilcari, H. Fan, M. Pink, D. J. Mindiola, Dalton Trans. 2010, 39, 358.
49. C. Kleeberg, L. Dang, Z. Lin, T. B. Marder, Angew. Chem. 2009, 121, 5454
50. Angew. Chem. Int. Ed. 2009, 48, 5350.
51. G. te Velde, F. M. Bickelhaupt, E. J. Baerends, C. Fonseca Guerra, S. J. A. Van Gisbergen, J. G. Snijders, T. Ziegler, J. Comput. Chem. 2001, 22, 931.
52. C. Fonseca Guerra, J. G. Snijders, G. te Velde, E. J. Baerends, Theor. Chem. Acc. 1998, 99, 391.
53. D. H. Ess, S. E. Wheeler, R. G. Iafe, L. Xu, N. Çelebi- ölçüm, K. N. Houk, Angew. Chem. 2008, 120, 7704
54. Angew. Chem. Int. Ed. 2008, 47, 7592.