Low coordinate germanium(II) and tin(II) hydride complexes: Efficient catalysts for the hydroboration of carbonyl compounds

Journal of the American Chemical Society

Volumn 136, Issue 8, 2014, Pages 3028-3031

  Hadlington, Terrance J ^a   Hermann, Markus ^b   Frenking, Gernot ^b   Jones, Cameron ^a  

^a MONASH UNIVERSITY   (Australia)

^b PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST LOADINGS; EFFICIENT CATALYSTS; HYDRIDE COMPLEXES; HYDROBORATION; LOW-VALENT; METAL HYDRIDES; ORGANIC SYNTHESIS; TURNOVER FREQUENCY;

CARBONYL COMPOUNDS; GERMANIUM; HYDRIDES; TIN;

CATALYSTS;

CARBONYL DERIVATIVE; GERMANIUM II; METAL DERIVATIVE; TIN DERIVATIVE; TIN HYDRIDE II; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CATALYST; CHEMICAL PROCEDURES; CHEMICAL REACTION; HYDROBORATION; HYDROSILYLATION; TURNOVER TIME;

EID: 84896867597     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5006477     Document Type: Article

References (30)

1. Power, P. P. Chem. Rec. 2012, 12, 238
2. Mandal, K. S.; Roesky, H. W. Acc. Chem. Res. 2012, 45, 298
3. Power, P. P. Acc. Chem. Res. 2011, 44, 627
4. Asay, M.; Jones, C.; Driess, M. Chem. Rev. 2011, 111, 354
5. Yao, S.; Xiong, Y.; Driess, M. Organometallics 2011, 30, 1748
6. Martin, D.; Soleilhavoup, M.; Bertrand, G. Chem. Sci. 2011, 2, 389
7. Power, P. P. Nature 2010, 463, 171
8. N.B. Excellent progress has been made in the development of catalysis involving "normal oxidation state" p-block frustrated Lewis pairs. See, for example: Erker, G.; Stephan, D. W. Frustrated Lewis Pairs II: Expanding the Scope; Springer: Heidelberg, 2013.
9. Hadlington, T. J.; Hermann, M.; Li, J.; Frenking, G.; Jones, C. Angew. Chem., Int. Ed. 2013, 52, 10199
10. Hadlington, T. J.; Jones, C. Chem. Commun. 2014, 50, 2321
11. Spikes, G. H.; Fettinger, J. C.; Power, P. P. J. Am. Chem. Soc. 2005, 127, 12232
12. Frey, G. D.; Lavallo, V.; Donnadieu, B.; Schöller, W. W.; Bertrand, G. Science 2007, 316, 439
13. Cho, B. T. Chem. Soc. Rev. 2009, 38, 443
14. Togni, A.; Grützmacher, H. Catalytic Heterofunctionalization; Wiley-VCH: Weinheim, 2001.
15. Fu, G. C.; Evans, D. A. J. Org. Chem. 1990, 55, 5678
16. Koren-Selfridge, L.; Query, I. P.; Hanson, J. A.; Isley, N. A.; Guzei, I. A.; Clark, T. B. Organometallics 2010, 29, 3896
17. Khalimon, A. Y.; Farha, P.; Kuzmina, L. G.; Nikonov, G. I. Chem. Commun. 2012, 48, 455
18. Oluyadi, A. A.; Ma, S.; Muhoro, C. N. Organometallics 2013, 32, 70
19. Almqvist, F.; Torstensson, L.; Gudmundsson, A.; Frejd, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 376
20. Giffels, G.; Dreisbach, C.; Kragl, U.; Weigerding, M.; Waldmann, H.; Wandrey, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2005
21. Arrowsmith, M.; Hadlington, T. J.; Hill, M. S.; Kociok-Kohn, G. Chem. Commun. 2012, 48, 4567
22. Blake, A. J.; Cunningham, A.; Ford, A.; Teat, S. J.; Woodward, S. Chem.-Eur. J. 2000, 6, 3586
23. Takagi, N.; Sakaki, S. J. Am. Chem. Soc. 2013, 135, 8955
24. One report on the reduction of ketones using high loadings (10 mol%) of tin(II) triflate as a catalyst in the presence of a silane invoked the intermediacy of a tin(II) hydride in the reaction. No evidence for this proposal was presented. Lawrence, N. J.; Bushell, S. M. Tetrahedron Lett. 2000, 41, 4507
25. For a recent example, see: Fasulo, M. E.; Lipke, M. C.; Tilley, T. D. Chem. Sci. 2013, 4, 3882
26. Jana, A.; Roesky, H. W.; Schulzke, C. Dalton Trans. 2010, 39, 132
27. Jana, A.; Roesky, H. W.; Schulzke, C.; Döring, A. Angew. Chem., Int. Ed. 2009, 48, 1106
28. Jana, A.; Roesky, H. W.; Schulzke, C. Inorg. Chem. 2009, 48, 9543
29. Query, I. P.; Squier, P. A.; Larson, E. M.; Isley, N. A.; Clark, T. B. J. Org. Chem. 2011, 76, 6452
30. Sewell, L. J.; Huertos, M. A.; Dickinson, M. E.; Weller, A. S. Inorg. Chem. 2013, 52, 4509