Magnesium catalysis of imine hydroboration

Chemistry - A European Journal

Volumn 19, Issue 8, 2013, Pages 2776-2783

  Arrowsmith, Merle ^a   Hill, Michael S ^a   Kociok Köhn, Gabriele ^a  

^a University of Bath   (United Kingdom)

Author keywords

homogeneous catalysis; hydroboration; imines; magnesium; main group elements

Indexed keywords

ALDIMINES; ALKYL COMPLEXES; COORDINATION SPHERE; HOMOGENEOUS CATALYSIS; HYDROBORATION; IMINES; KETIMINES; KINETIC ANALYSIS; MAIN-GROUP ELEMENTS; PINACOLS; PRECATALYSTS; RATE-DETERMINING PROCESS;

AMIDES; CATALYSIS; MOLECULES; NITROGEN COMPOUNDS; REACTION KINETICS;

MAGNESIUM;

EID: 84873652696     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201203190     Document Type: Article

References (67)

1. M. Rueping, E. Sugiono, C. Azap, T. Theissmann, A. P. Antonchick, S. N. Khan, N. J. Cho, H.-S. Kim, Regio- and Stereo- Controlled Oxidations and Reductions, Vol. 5 (Eds.:, S. M. Roberts, J. Whittall,), Wiley, Hoboken, 2007, Chapter 4
2. Modern Reduction Methods (Eds.:, P. G. Andersson, I. J. Munslow,), Wiley, Hoboken, 2008
3. M. Figlus, Recoverable Catalysts for Asymmetric Reduction of Imines: Synthesis and Evaluation of Activities, Verlag Dr. Müller, Saarbrücken, 2010; for general reviews on imine reduction, see
4. J. F. Carpentier, V. Bette, Curr. Org. Chem. 2002, 6, 913
5. O. Riant, N. Mostefai, J. Courmarcel, Synthesis 2004, 2943
6. S. Díez-González, S. P. Nolan, Org. Prep. Proc. Int. 2007, 39, 523
7. C. G. Arena, Mini-Rev. Org. Chem. 2009, 6, 159
8. T. C. Nugent, M. El-Shazly, Adv. Synth. Catal. 2010, 352, 753
9. Z. Wang, Z. Jiang, Asia J. Chem. 2010, 22, 4141
10. S. Guizzetti, M. Benaglia, Eur. J. Org. Chem. 2010, 5529
11. J. G. De Vries, N. Mrsic, Catal. Sci. Technol. 2011, 1, 727
12. J. Xie, S. Zhu, Q. Zhou, Chem. Rev. 2011, 111, 1713
13. Z. Yu, W. Jin, Q. Jiang, Angew. Chem. Int. Ed. 2012, 51, 6060.
14. S. Guizzetti, M. Benaglia, F. Cozzi, R. Annunziata, Tetrahedron 2009, 65, 6354
15. D. T. Hog, M. Oestreich, Eur. J. Org. Chem. 2009, 5047
16. A. V. Malkov, K. Vranková, R. C. Sigerson, S. Stončius, P. Kočovský, Tetrahedron 2009, 65, 9481
17. B. Li, C. B. Bheeter, C. Darcel, P. H. Dixneuf, ACS Catal. 2011, 1, 1221
18. L. C. M. Castro, J.-B. Sortais, C. Darcel, Chem. Commun. 2012, 48, 151
19. J. Koller, R. G. Bergman, Organometallics 2012, 31, 2530.
20. R. T. Baker, J. C. Calabrese, S. A. Wescott, J. Organomet. Chem. 1995, 498, 109
21. Z. H. Lu, N. Bhongle, X. P. Su, S. Ribe, C. H. Senanayake, Tetrahedron Lett. 2002, 43, 8617
22. E. H. M. Kirton, G. Tughan, R. E. Morris, R. A. Field, Tetrahedron Lett. 2004, 45, 853
23. L. Koren-Selfridge, H. N. Londino, J. K. Vellucci, B. J. Simmons, C. P. Casey, T. B. Clark, Organometallics 2009, 28, 2085
24. M. Tokizane, K. Sato, Y. Sakami, Y. Imori, C. Matsuo, T. Ohta, Y. Ito, Synthesis 2010, 36; for recent research of borane-based frustrated Lewis pair imine hydrogenation, see
25. P. A. Chase, G. C. Welch, T. Jurca, D. W. Stephan, Angew. Chem. 2007, 119, 8196
26. Angew. Chem. Int. Ed. 2007, 46, 8050
27. P. A. Chase, T. Jurca, D. W. Stephan, Chem. Commun. 2008, 1701
28. P. Spies, G. Erker, G. Kehr, K. Bergander, R. Froehlich, S. Grimme, D. W. Stephan, Chem. Commun. 2007, 5072
29. Z. M. Heiden, D. W. Stephan, Chem. Commun. 2011, 47, 5729
30. G. Ghattas, D. Chen, F. Panb, J. Klankermayer, Dalton Trans. 2012, 41, 9026; for a recent example of catalytic imine hydrogenation based on a borenium cation, see
31. P. Eisenberger, A. M. Bailey, C. M. Crudeen, J. Am. Chem. Soc. 2012, 134, 17384.
32. D. Guijarro, O. Pablo, M. Yus, J. Org. Chem. 2010, 75, 5265
33. M. Dürrenberger, T. Heinisch, Y. M. Wilson, T. Rossel, E. Nogueira, E. Knörr, A. Mutschler, K. Kersten, M. J. Zimbron, J. Pierron, T. Schirmer, T. R. Ward, Angew. Chem. 2011, 123, 3082
34. Angew. Chem. Int. Ed. 2011, 50, 3026
35. J. M. Farrell, Z. M. Heiden, D. W. Stephan, Organometallics 2011, 30, 4497
36. N. Pannetier, J.-B. Sortais, J.-T. Issenhuth, L. Barloy, C. Sirlin, A. Holuigue, L. Lefort, L. Panella, J. G. de Vries, M. Pfeffer, Adv. Synth. Catal. 2011, 353, 2844
37. T. D. Nixon, M. K. Whittlesey, J. M. J. Williams, Tetrahedron Lett. 2011, 52, 6652.
38. A. Fabrello, A. Bachelier, M. Urrutigoity, P. Kalck, Coord. Chem. Rev. 2010, 254, 273
39. N. Fleury-Brégeot, V. de La Fuente, S. Castillon, C. Claver, ChemCatChem 2010, 2, 1346
40. C. Wang, B. Villa-Marcos, J. Xiao, Chem. Commun. 2011, 47, 9773
41. S. Werkmeister, S. Fleischer, S. Zhou, M. Beller, ChemSusChem 2012, 5, 777.
42. E. Lu, Y. Chen, X. Leng, Organometallics 2011, 30, 5433
43. M. E. Burin, A. A. Logunov, N. O. Druzhkov, G. K. Fukin, M. N. Bochkarev, Russ. Chem. Bull. 2011, 60, 1586; For catalytic reactivity, see
44. C. A. Willoughby, S. L. Buchwald, J. Org. Chem. 1993, 58, 7627
45. N. E. Lee, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 5985
46. C. A. Willoughby, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 8952
47. C. A. Willoughby, S. L. Buchwald, J. Am. Chem. Soc. 1994, 116, 11703
48. J. Okuda, S. Verch, R. Sturmer, T. P. Spaniol, J. Organomet. Chem. 2000, 605, 55
49. K. Takaki, K. Komeyama, K. Takehira, Tetrahedron 2003, 59, 10381
50. H. Gruber-Woelfler, J. G. Khinast, M. Flock, R. C. Fischer, J. Sassmannshausen, T. Stanoeva, G. Gescheidt, Organometallics 2009, 28, 2546.
51. A. G. M. Barrett, M. R. Crimmin, M. S. Hill, P. A. Procopiou, Proc. R. Soc. London Ser. A 2010, 466, 927
52. S. Harder, Chem. Rev. 2010, 110, 3852.
53. J. Spielmann, F. Buch, S. Harder, Angew. Chem. 2008, 120, 9576
54. Angew. Chem. Int. Ed. 2008, 47, 9434
55. J. Spielmann, S. Harder, Eur. J. Inorg. Chem. 2008, 1480
56. F. Buch, J. Brettar, S. Harder, Angew. Chem. 2006, 118, 2807
57. Angew. Chem. Int. Ed. 2006, 45, 2741.
58. M. Arrowsmith, T. Hadlington, M. S. Hill, G. Kociok-Köhn, Chem. Commun. 2012, 48, 4567.
59. M. Arrowsmith, M. S. Hill, T. Hadlington, G. Kociok-Köhn, C. Weetman, Organometallics 2011, 30, 5556.
60. S. W. Hadebe, R. S. Robinson, Eur. J. Org. Chem. 2006, 4898
61. W. Clegg, A. J. Scott, C. Dai, L. Chaoyang, G. Lesley, T. B. Marder, N. C. Norman, L. J. Farrugia, Acta Crystallogr. Sect. C 1996, 52, 2545.
62. A. P. Dove, V. C. Gibson, P. Hormnirun, E. L. Marshall, J. A. Segal, A. J. P. White, D. J. Williams, Dalton Trans. 2003, 3088.
63. M. R. Crimmin, M. Arrowsmith, A. G. M. Barrett, I. J. Casely, M. S. Hill, P. A. Procopiou, J. Am. Chem. Soc. 2009, 131, 9670
64. M. Arrowsmith, M. R. Crimmin, A. G. M. Barrett, M. S. Hill, G. Kociok-Köhn, P. A. Procopiou, Organometallics 2011, 30, 1493.
65. A. G. M. Barrett, C. Brinkmann, M. R. Crimmin, M. S. Hill, P. Hunt, P. A. Procopiou, J. Am. Chem. Soc. 2009, 131, 12906
66. C. Brinkmann, A. G. M. Barrett, M. S. Hill, P. A. Procopiou, J. Am. Chem. Soc. 2012, 134, 2193.
67. E. V. Anslyn, D. A. Dougherty, Modern Physical Organic Chemistry, University Science Books, Sausalito, 2006.