B. Desai, T. N. Danks / Tetrahedron Letters 42 (2001) 5963–5965
5965
In conclusion, it has been shown that a formate sup-
ported on an Amberlite resin may be used as a poly-
Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.;
Jacquault, P.; Mathe, D. Synthesis 1998, 1213.
®
mer-supported source for transfer hydrogenation
reactions using Wilkinson’s catalyst under thermal and
microwave conditions.
3. (a) Rylander, P. N. Hydrogenation Methods; Academic
Press: Orlando, FL, 1985; (b) James, B. R. Homogenous
Hydrogenation; Wiley: NewYork, 1973.
4
. Banik, B. K.; Barakat, K. J.; Wagle, D. R.; Manhar, M.
S.; Bose, A. K. J. Org. Chem. 1999, 64, 5746.
. (a) Anwer, M. K.; Sherman, D. B.; Roney, J. G.; Spatola,
A. F. J. Org. Chem. 1989, 54, 1284; (b) Anwer, M. K.
Tetrahedron Lett. 1985, 26, 1381; (c) Rajagopal, S.; Spa-
tola, A. F. Appl. Catal. A 1997, 152, 69.
The application of this chemistry for catalytic reduction
of electron-rich alkenes, debenzylations, and asymmet-
ric hydrogenation reactions is currently under investiga-
tion.
5
6
7
8
. Al-Qahtani, M. H.; Cleator, N.; Danks, T. N.; Garman,
R. N.; Jones, J. R.; Stefaniak, S.; Morgan, A. D.; Sim-
monds, A. J. J. Chem. Res. 1998, 26, 400.
. Resin loading was determined as 2.5 mmol g by poten-
tiometric titration after releasing the formate as formic
acid by washing with dil. HCl.
Acknowledgements
−
1
We thank the Personal Chemistry AB for financial
support and provision of
microwave reactor.
a
MW-10 Microwell
. In a typical experiment, E-3-phenylpropenoic acid (0.025
®
g, 0.16 mmol), Amberlite IRA 938-supported formate
(
0.200 g) and Wilkinson’s catalyst (0.04 g, 0.0043 mmol)
References
were suspended in a reaction tube using DMSO (0.5 ml) as
the solvent. The mixture was irradiated with microwaves
at 100 W for 30 s. On cooling the mixture was diluted with
dichloromethane (5 ml) and filtered. The filtrate was
washed with water (2×5 ml). The organic fraction was
1
. (a) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P.
S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J.
S.; Store, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans.
1
2000, 3815; (b) Kirschning, A.; Monenschein, H.; Wit-
dried over magnesium sulfate (MgSO ) and the solvent
tenberg, R. Angew. Chem., Int. Ed. 2001, 40, 650.
. (a) Caddick, S. Tetrahedron 1995, 51, 10403; (b) Deshayes,
S.; Liagre, M.; Loupy, A.; Luche, J. L.; Petit, A. Tetra-
hedron 1999, 55, 10851; (c) de la Hoz, A.; D ´ı az-Ortiz, A.;
Moreno, A.; Langa, F. Eur. J. Org. Chem. 2000, 3659; (d)
4
2
removed under reduced pressure to give a reddish-orange
residue which was purified by filtration through a plug of
alumina to give 3-phenylpropanoic acid as white crystals
(0.024 g, 95%).
.