Poly(diallyldimethylammonium chloride) resin was used as an efficient polymeric phase transfer catalyst, which catalyzed the chemoselective reduction of aldehydes and ketones by NaBH₄ to give the corresponding alcohols in high yields under solvent-free conditions.

REFERENCES

1a Tanaka, K., Solvent-Free Organic Synthesis, Wiley, Weinheim, 2003.
10.1002/3527601821
Google Scholar
1b Hodnett, B. K.; Kybett, A. P.; Clark, J. H.; Smith, K., Supported Reagents and Catalysts in Chemistry, RSC, Cambridge, 1998.
Google Scholar
2a Montanari, F.; Landini, D.; Rolla, F.. Top. Curr. Chem., 1982, 101, 145.
Google Scholar
2b Dehmlow, V. V.; Dehmlow, S. S., Phase Transfer Catalysis, Verlag Chemie, Weinheim, Germany, 1993.
Google Scholar
3a Montana, F.; Tundo, P.. J. Org. Chem., 1981, 46, 2125.
10.1021/jo00323a029
Web of Science® Google Scholar
3b Funkunishi, K.; Czech, B.; Regen, S. L.. J. Org. Chem., 1981, 46, 148.
Google Scholar
4a Brown, H. C., Boranes in Organic Chemistry, Cornell University Press, Ithaca, 1972.
10.7591/9781501741432
Google Scholar
4b Brown, H. C.; Krishnamurthy, R.. Tetrahedron, 1979, 35, 567.
10.1016/0040-4020(79)87003-9
CAS Web of Science® Google Scholar
4c Grilble, G. W.; Nataitis, C. F.. Org. Prep. Proced. Int., 1985, 17, 317.
10.1080/00304948509355522
Web of Science® Google Scholar
5 Tamami, B.; Mahdavi, H.. Tetrahedron, 2003, 59, 821.
10.1016/S0040-4020(02)01588-0
CAS Web of Science® Google Scholar
6 Mahdavi, H.; Haghani, E.; Malakian, B.. React. Funct. Polym., 2006, 66, 1033.
10.1016/j.reactfunctpolym.2006.01.011
CAS Web of Science® Google Scholar
7 Ward, D. E.; Rhee, C. H.. Synth. Commun., 1988, 18, 1927.
10.1080/00397918808068259
CAS Web of Science® Google Scholar
8a Johnson, M. R.; Rickborn, B.. J. Org. Chem., 1970, 35, 1041.
10.1021/jo00829a039
CAS Web of Science® Google Scholar
8b Wilson, K. E.; Seinder, R. T.; Masamune, S.. J. Chem. Soc., Chem. Commun., 1970, 213.
10.1039/c2970000213b
CAS Google Scholar
8c Sande, A. R.; Jagadale, M. H.; Mane, B. M.; Salunkhe, R.. Tetrahedron Lett., 1984, 25, 3501.
10.1016/S0040-4039(01)91059-7
CAS Web of Science® Google Scholar
9 Nutaitis, C. F.; Bernardo, J. E.. J. Org. Chem., 1989, 54, 5629.
10.1021/jo00284a046
CAS Web of Science® Google Scholar
10a Fujii, H.; Oshima, K.; Utimato, K.. Chem. Lett., 1991, 1847.
10.1246/cl.1991.1847
CAS Web of Science® Google Scholar
10b Fleet, G. W. J.; Harding, P. J. C.. Tetrahedron Lett., 1981, 22, 675.
10.1016/S0040-4039(01)92520-1
CAS Web of Science® Google Scholar
11 Firouzabadi, H.; Zeynizadeh, F.. Iran. J. Sci. Technol., Trans. A, 1995, 19, 103.
CAS Google Scholar
12a Firouzabadi, H.; Zeynizadeh, F.. Bull. Chem. Soc. Jpn., 1996, 69, 1 and the references cited therein.
10.1246/bcsj.69.685
Web of Science® Google Scholar
12b Hudlicky, M., Reduction in Organic Chemistry, Ellis Horwood LTD., Chichester, 1984.
Google Scholar
13 Yakabe, S.; Hirano, M.. Can. J. Chem., 1998, 76, 1916.
10.1139/v98-204
Web of Science® Google Scholar
14 Yoon, N. M.; Park, K. B.; Gyoung, Y. S.. Tetrahedron Lett., 1983, 24, 5367.
10.1016/S0040-4039(00)87870-3
CAS Web of Science® Google Scholar
15 Sohmiya, H.; Kimura, T.; Fujita, M.; Ando, T.. Tetrahedron, 1998, 54, 13737.
10.1016/S0040-4020(98)00844-8
CAS Web of Science® Google Scholar

Citing Literature

Volume26, Issue2

February, 2008

Pages 333-337

Poly(diallyldimethylammonium chloride) as an Efficient Phase Transfer Catalyst in Solvent-Free Reduction of Carbonyl Compounds with NaBH₄

Abstract

REFERENCES

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

Poly(diallyldimethylammonium chloride) as an Efficient Phase Transfer Catalyst in Solvent-Free Reduction of Carbonyl Compounds with NaBH4

Abstract

REFERENCES

Citing Literature

References

Related

Information

Poly(diallyldimethylammonium chloride) as an Efficient Phase Transfer Catalyst in Solvent-Free Reduction of Carbonyl Compounds with NaBH₄