Efficient solvent-free selective monoalkylation of arylacetonitriles with mono-, bis-, and tris-primary alcohols catalyzed by a Cp*Ir complex

Journal of Organic Chemistry

Volumn 71, Issue 21, 2006, Pages 8023-8027

  Löfberg, Christian ^a   Grigg, Ronald ^a   Whittaker, Mark A ^a   Keep, Ann ^b   Derrick, Andrew ^c  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b JOHNSON MATTHEY TECHNOLOGY CENTRE   (United Kingdom)

^c PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLACETONITRILES; MONOALKYLATION;

ALCOHOLS; CATALYST ACTIVITY; MICROWAVE HEATING; REDOX REACTIONS; SOLVENTS; SUBSTITUTION REACTIONS;

ACETONITRILE;

ACETONITRILE DERIVATIVE; ALCOHOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ALKYLATION; ARTICLE; ATOM; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; MICROWAVE COOKING; MONOALKYLATION; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; THIN LAYER CHROMATOGRAPHY;

ACETONITRILES;

EID: 33750019444     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061113p     Document Type: Article

References (38)

1. Reviews: (a) Alcaide, B.; Almendros, P. Eur. J. Org. Chem. 2002, 1595.
2. (b) List, B. Tetrahedron 2002, 58, 5573.
3. Grigg, R.; Mitchell, T. R. B.; Sutthivaiyakit, S.; Tongpenyai, N. Tetrahedron Lett. 1981, 22, 4107.
4. (a) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.; J. Am. Chem. Soc. 1989, 111, 5954.
5. (b) Murahashi, S.I.; Naota, T.; Taki, H.; Mizuno, M.; Takaya, H.; Komiya, S.; Mizuho, Y.; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. J. Am. Chem. Soc. 1995, 117, 12436.
6. (c) Murahashi, S.-I.; Takaya, H. Acc. Chem. Res. 2000, 33, 225.
7. (a) Kulp, S. S.; McGee, M. J. J. Org. Chem. 1983, 48, 4097.
8. (b) Hartmann, R. W.; Batzl, C. J. Med. Chem. 1986, 29, 1362.
9. (c) Im, D. S.; Cheong, C. S.; Lee, S. H.; Youn, B. H.; Kim, S. C. Tetrahedron 2000, 56, 1309.
10. (d) Wu, Z.-L.; Li, Z.-Y. Tetrahedron: Asymmetry 2001, 12, 3305.
11. (e) Takaya, H.; Yoshida, K.; Isozaki, K.; Terai, H.; Murahashi, S.-I. Angew. Chem., Int. Ed. 2003, 42, 3302.
12. (a) Grigg, R.; Hasakunpaisarn, A.; Kilner, C.; Kongkathip, B.; Kongkathip, N.; Pettman, A.; Sridharan, V. Tetrahedron 2005, 61, 9356.
13. (b) Bromidge, S. M.; Brown, F.; Cassidy, F.; Clark, M. S. G.; Dabbs, S.; Hawkins, J.; Loudon, J. M.; Orlek, B. S.; Riley, G. J. Bioorg. Med. Chem. Lett. 1992, 2, 791.
14. (c) Dei, S.; Romanelli, M. N.; Scapecchi, S.; Teodori, E.; Chiarini, A.; Gualtieri, F. J. Med. Chem. 1991, 34, 2219.
15. (a) Ivanov, C.; Markov, P.; Amaudov, M. Chem. Ber. 1967, 100, 690.
16. (b) Normant, H.; Cuviguy, T. Bull. Soc. Chim. France 1965, 1881.
17. (c) Schwachhofer, G.; Chopin, J. Bull. Soc. Chim. France 1962, 835.
18. (a) Kenyon, W. G.; Kaiser, E. M.; Hauser, C. R. J. Org. Chem. 1965, 30, 4135.
19. (b) Cloke, J. B.; Leary, T. S. J. Am. Chem. Soc. 1945, 67, 1249.
20. (c) Lyle, R. E.; Lyle, G. G. J. Am. Chem. Soc. 1952, 74, 4059.
21. Black, P. J.; Harris, W.; Williams, J. M. J. Angew. Chem., Int. Ed. 2001, 40, 4475.
22. Motokura, K.; Nishimura, D.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2004, 126, 5662.
23. Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. J. Org. Chem. 2001, 66, 9020.
24. Cho, C. S.; Kim, B. T.; Kim. T.-J.; Shim, S. C. Tetrahedron Lett. 2002, 43, 7987.
25. Taguchi, K.; Nakagawa, H.; Hirabayashi, T.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2004, 126, 72.
26. Edwards, M. G.; Williams, J. M. J. Angew. Chem., Int. Ed. 2002, 41, 4740.
27. 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.
28. Black, P. J.; Cami-Kobeci, G.; Edwards, M. G.; Slatford, P. A.; Whittlesey, M. K.; Williams, J. M. J. Org. Biomol. Chem. 2006, 4, 116.
29. (a) Abramovitch, R. A. Org. Prep. Proced. Int., 1991, 23, 685.
30. (b) Caddick, S. Tetrahedron 1995, 51, 10403.
31. (a) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213.
32. (b) Varma, R. S. Green Chem. 1999, 43.
33. (a) Loupy, A.; Perreux, L.; Petit, A. Ceram. Trans. 2001, 111, 163.
34. (b) Varma, R. S. Pure Appl. Chem. 2001, 73, 193.
35. Microreview: (a) Simon, C.; Constantieux, T.; Rodriguez, J. Eur. J. Chem. 2004, 4957.
36. (b) Sabitha, G.; Fatima, N.; Venkata Reddy, E.; Yadav, J. S. Adv. Synth. Catal. 2005, 347, 1353.
37. Review: Fujita, K.; Yamaguchi, R. Synlett 2005, 4, 560.
38. Barbry, D.; Pasquier, C.; Faven, C. Synth. Commun. 1995, 25, 19, 3007.