Barium-Mediated Cross-Dehydrocoupling of Hydrosilanes with Amines: A Theoretical and Experimental Approach

Angewandte Chemie - International Edition

Volumn 54, Issue 26, 2015, Pages 7679-7683

  Bellini, Clément ^a   Carpentier, Jean François ^a   Tobisch, Sven ^b   Sarazin, Yann ^a  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

^b UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

alkaline earth metals; amines; barium; density functional calculations; reaction mechanisms

Indexed keywords

ALKALINE EARTH METALS; AMINES; DENSITY FUNCTIONAL THEORY;

ALKALINE EARTH; CHEMO-SELECTIVITY; DEHYDROCOUPLINGS; EXPERIMENTAL APPROACHES; HYDROGEN TRANSFER; METAL CENTERS; NUCLEOPHILIC ATTACK; REACTION MECHANISM;

BARIUM;

EID: 85027928263     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201502956     Document Type: Article

References (37)

1. M. Lappert, P. P. Power, A. Protchenko, A. Seeber, Metal Amide Chemistry, Wiley, Chichester, 2009.
2. L. F. Fieser, M. Fieser, Reagents in Organic Chemistry, Wiley, New York, 1967.
3. Y. Tanabe, T. Misaki, M. Kurihara, A. Iida, Y. Nishii, Chem. Commun. 2002, 1628.
4. D. W. Robbins, T. A. Boebel, J. F. Hartwig, J. Am. Chem. Soc. 2010, 132, 4068
5. S. Itagaki, K. Kamata, K. Yamaguchi, N. Mizuno, Chem. Commun. 2012, 48, 9269
6. C. D. F. Königs, M. F. Müller, N. Aiguabella, H. F. T. Klare, M. Oestreich, Chem. Commun. 2013, 49, 1506
7. L. Greb, S. Tamke, J. Paradies, Chem. Commun. 2014, 50, 2318.
8. D. Seyferth, G. H. Wiseman, J. Am. Ceram. Soc. 1984, 67, C 132
9. Y. D. Blum, K. B. Schwartz, R. M. Laine, J. Mater. Sci. 1989, 24, 1707
10. H. Q. Liu, J. F. Harrod, Organometallics 1992, 11, 822
11. N. R. Dando, A. J. Perrotta, C. Strohmann, R. M. Stewart, D. Seyferth, Chem. Mater. 1993, 5, 1624
12. M. Birot, J.-P. Pilot, J. Dunoguès, Chem. Rev. 1995, 95, 1443.
13. R. Fessenden, J. S. Fessenden, Chem. Rev. 1961, 61, 361.
14. L. H. Sommer, J. D. Citron, J. Org. Chem. 1967, 32, 2470
15. Y. Blum, R. M. Laine, Organometallics 1986, 5, 2081
16. C. Biran, Y. D. Blum, R. Glaser, D. S. Tse, K. A. Youngdahl, R. M. Laine, J. Mol. Catal. 1988, 48, 183
17. E. J. Matarasso-Tchiroukhine, Chem. Soc. Chem. Commun. 1990, 681
18. W. D. Wang, R. Eisenberg, Organometallics 1991, 10, 2222
19. C. K. Toh, H. T. Poh, C. S. Lim, W. Y. Fan, J. Organomet. Chem. 2012, 717, 9.
20. A. Kawachi, M. Zaima, A. Tani, Y. Yamamoto, Chem. Lett. 2007, 36, 362.
21. L.K. Allen, R. Garcia-Rodriquez, D. S Wright, Dalton Trans. 2015, DOI:.
22. K. Takaki, T. Kamata, Y. Miura, T. Shishido, K. Takehira, J. Org. Chem. 1999, 64, 3891
23. F. Buch, S. Harder, Organometallics 2007, 26, 5132
24. W. Xie, H. Hu, C. Cui, Angew. Chem. Int. Ed. 2012, 51, 11141
25. Angew. Chem. 2012, 124, 11303.
26. J. X. Wang, A. K. Dash, J.-C. Berthet, M. Ephritikhine, M. S. Eisen, J. Organomet. Chem. 2000, 49, 610.
27. T. Tsuchimoto, Y. Iketani, M. Sekine, Chem. Eur. J. 2012, 18, 9500.
28. J. F. Dunne, S. R. Neal, J. Engelkemier, A. Ellern, A. D. Sadow, J. Am. Chem. Soc. 2011, 133, 16782
29. M. S. Hill, D. J. Liptrot, D. J. MacDougall, M. F. Mahon, T. P. Robinson, Chem. Sci. 2013, 4, 4212.
30. A. G. M. Barrett, C. Brinkmann, M. R. Crimmin, M. S. Hill, P. Hunt, P. A. Procopiou, J. Am. Chem. Soc. 2009, 131, 12906
31. M. Arrowsmith, M. R. Crimmin, A. G. M. Barrett, M. S. Hill, G. Kociok-Köhn, P. A. Procopiou, Organometallics 2011, 30, 1493
32. C. Brinkmann, A. G. M. Barrett, M. S. Hill, P. A. Procopiou, J. Am. Chem. Soc. 2012, 134, 2193
33. B. Liu, T. Roisnel, J.-F. Carpentier, Y. Sarazin, Angew. Chem. Int. Ed. 2012, 51, 4943
34. Angew. Chem. 2012, 124, 5027
35. B. Liu, T. Roisnel, J.-F. Carpentier, Y. Sarazin, Chem. Eur. J. 2013, 19, 13445
36. S. Tobisch, Chem. Eur. J. 2014, 20, 8988
37. S. Tobisch, Chem. Eur. J. 2015, 21, 6765.