Benzyl alcohol as an alkylating agent using the ruthenium-catalyzed borrowing hydrogen strategy (4,4-dimethyl-3-oxo-2-benzylpentanenitrile)

Organic Syntheses

Volumn 86, Issue , 2009, Pages 28-35

  Nixon, Tracy D ^a,d   Slatford, Paul A ^a   Whittlesey, Michael K ^a,e   Williams, Jonathan M J ^a,c   Candito, David A ^b   Lautens, Mark ^b  

^a University of Bath   (United Kingdom)

^b UNIVERSITY OF TORONTO   (Canada)

^c UNIVERSITY OF BATH   (United Kingdom)

^d UNIVERSITY OF LEEDS   (United Kingdom)

^e UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 69249205266     PISSN: 00786209     EISSN: 16000730     Source Type: Book Series    
DOI: 10.15227/orgsyn.086.0028     Document Type: Article

References (21)

1. Ahmad, N.; Levison, J. J.; Robinson, S. D.; Uttley, M. F. Inorg. Synth. 1974,15, 45-64.
2. Binovi, L. J.; ArIt, H. G. J. Org. Chem. 1961, 26, 1656-1657.
3. Examples of Ru catalysts; (a) Grigg, R.; Mitchell, T. R. B.; Sutthivaiyakit, S.; Tongpenyai, N. Tetrahedron Lett. 1981, 22, 4107-4110;
4. (b) Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. J. Org. Chem. 2001, 66, 9020-9022;
5. c) Motokura, K.; Nishimura, D.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc, 2004, 126, 5662-5663;
6. d) Martinez, R.; Brand, G. J.; Ramón, D. J.; Yus, M. Tetrahedron Lett. 2005, 46, 3683-3686;
7. (e) Edwards, M. G.; Jazzar, R. F. R.; Paine, B. M.; Shermer, D. J.; Whittlesey, M. K.; Williams, J. M. J.; Edney, D. D. Chem. Commun. 2004, 90-91;
8. (f) Burling, S.; Paine, B. M.; Nama, D.; Brown, V. S.; Mahon, M. F.; Prior, T. J.; Pregosin, P. S.; Whittlesey, M. K.; Williams, J. M. J. J. Am. Chem. Soc. 2007, 129, 1987-1995.
9. Examples of Ir catalysts; (a) Fujita, K.; Yamaguchi, R. Synlett 2005, 560-571;
10. (b) Löfberg, C.; Grigg, R.; Keep, A.; Derrick, A.; Sridharan, V.; Kilner, C. Chem. Commun. 2006, 5000-5002;
11. c) Morita, M.; Obora, Y.; Ishii, Y. Chem. Commun. 2007, 2850-2852;
12. d) Edwards, M. G.; Williams, J. M. J. Angew. Chem. Int. Ed. 2002, 41, 4740-4743.
13. For reviews of the borrowing hydrogen approach, see; (a) Guillena, G.; Ramón, D. J.; Yus, M. Angew. Chem. Int. Ed. 2007, 46, 2358-2364;
14. (b) Hamid, M. H. S. A.; Slatford, P. A.; Williams, J. M. J. Adv. Synth. Catal. 2007, 349, 1555-1575.
15. (a) Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Ace. Chem. Res. 2001, 34, 895-904;
16. b) Freixa, Z.; van Leeuwen, P. W. N. M. Dalton Trans. 2003, 1890-1901.
17. Slatford, P. A.; Whittlesey, M. K.; Williams, J. M. J., Tetrahedron Lett., 2006, 47, 6787-6789.
18. Ledger, A. E. W.; Slatford, P. A.; Lowe, J. P.; Mahon, M. F.; Whittlesey, M. K.; Williams, J. M. J. Dalton Trans., submitted.
19. Anand, N.; Owston, N. A.; Parker, A. J.; Slatford, P. A.; Williams, J. M. J. Tetrahedron Lett. 2007, 48, 7761-7763.
20. Pridmore, S. J.; Slatford, P. A.; Williams, J. M. J. Tetrahedron Lett. 2007, 48, 5111-5114.
21. Pridmore, S. J.; Slatford, P. A.; Daniel, A.; Whittlesey, M. K.; Williams, J. M. J. Tetrahedron Lett. 2007, 48, 5115-5120.