Radical addition of alkyl halides to formaldehyde in the presence of cyanoborohydride as a radical mediator. A new protocol for hydroxymethylation reaction

Journal of the American Chemical Society

Volumn 134, Issue 2, 2012, Pages 875-877

  Kawamoto, Takuji ^a   Fukuyama, Takahide ^a   Ryu, Ilhyong ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKOXY RADICALS; ALKYL HALIDES; ALKYL RADICAL ADDITION; HYDROBORATES; HYDROGEN SOURCES; HYDROXYMETHYLATION; NEW PROTOCOL; PARAFORMALDEHYDES; RADICAL ADDITION; RADICAL CHAIN MECHANISMS; SYNTHONS; TETRABUTYLAMMONIUM;

ACETAL RESINS; HYDROGEN; MECHANISMS;

FORMALDEHYDE;

ANION; BORANE DERIVATIVE; BROMIDE; CYANOBOROHYDRIDE SODIUM; FORMALDEHYDE; HALIDE; HALOGENOALKANE; HYDROGEN; IODIDE; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; METHYLATION; RADICAL REACTION; STEREOCHEMISTRY;

EID: 84855927060     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja210585n     Document Type: Article

References (29)

1. Kleinman, E. F. In Comprehensive Organic Synthesis, 1 st ed.; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 2, p 893.
2. Kobayashi, S.; Mori, Y.; Fossey, J. S.; Salterm, M. M. Chem. Rev. 2011, 111, 2626
3. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811
4. Fuller, G.; Rust, F. F. J. Am. Chem. Soc. 1958, 80, 6148
5. Oyama, M. J. Org. Chem. 1965, 30, 2429
6. Kollar, J. U.S. Patent 4 393 252, 1983.
7. Kollar, J. U.S. Patent 4 337 371, 1982.
8. Kollar, J. U.S. Patent 4 412 085, 1983.
9. Kollar, J. CHEMTECH 1984, 504
10. Sanderson, J. S.; Yeakey, E. L.; Lin, J. J.; Duranleau, R.; Marquis, E. T. J. Org. Chem. 1987, 52, 3243
11. Sanderson, J. S.; Yeakey, E. L.; Lin, J. J.; Duranleau, R.; Marquis, E. T. J. Org. Chem. 1988, 53, 2859
12. Miyaura, N.; Itoh, M.; Suzuki, A.; Brown, H. C.; Midland, M. M.; Jacob, P., III J. Am. Chem. Soc. 1972, 94, 6549
13. For radical disconnection approach, see: Curran, D. P. Synlett 1991, 63
14. Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177
15. Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991
16. Kim, S.; Kim, S. Bull. Chem. Soc. Jpn. 2007, 80, 809
17. Miyabe, H.; Yoshioka, H.; Kohtani, S. Curr. Org. Chem. 2010, 14, 1254
18. Koabayashi, S.; Kawamoto, T.; Uehara, S.; Fukuyama, T.; Ryu, I. Org. Lett. 2010, 12, 1548
19. For tin-free Giese reaction using cyanoborohydride reagents, see: Ryu, I.; Uehara, S.; Hirao, H.; Fukuyama, T. Org. Lett. 2008, 10, 1005
20. Giles, J. R. M.; Roberts, B. P. J. Chem. Soc., Chem. Commun. 1981, 360
21. Giles, J. M.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1982, 1699
22. Baban, J. A.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1988, 1195
23. Barton, D. H. R.; Jacob, M. Tetrahedron Lett. 1998, 39, 1331
24. Ueng, S.-H.; Solovyev, A.; Yuan, X.; Geib, S. J.; Fensterbank, L.; Lacote, E.; Malacria, M.; Newcomb, M.; Walton, J. C.; Curran, D. P. J. Am. Chem. Soc. 2009, 131, 11256
25. For recent review of NHC-borane, see: Curran, D. P.; Solovyev, A.; Brahmi, M. M.; Fensterbank, L.; Malacria, M.; Lacote, E. Angew. Chem., Int. Ed. 2011, 50, 10294
26. For a kinetic study on halogen atom abstraction by borane radical anion, see: Sheeller, B.; Ingold, K. U. J. Chem. Soc., Perkin Trans. 2 2001, 480
27. Barltrop, J. A.; Bradbury, D. J. Am. Chem. Soc. 1973, 95, 5085
28. Kropp, M.; Schuster, G. B. Tetrahedron Lett. 1987, 28, 5295
29. Liu, Q.; Han, B.; Zhang, W.; Yang, L.; Liu, Z.; Yu, W. Synlett 2005, 2248