An efficient liquid-phase synthesis of trans-cinnamic acids with good yields and high purities on soluble polymer support has been developed by treatment of poly(ethylene glycol) bound acrylate with aryl iodides in the presence of catalytic amounts of palladium acetate and tetra-n-butylammonium bromide in water using potassium carbonate as a base, and subsequent cleavage from the PEG.
(a) WilsonS.R., and CzarnikA. W.Combinatorial Chemistry: Synthesis and application; John Wiley & Sons: New York, 1997.
2.
ThompsonL.A., and EllmanJ. A., Chem. Rev., 1996, 96, 555.
3.
LamK.S., LeblM., and Krchn˘ákV., Chem. Rev., 1997, 97, 411.
4.
ShuttleworthS.J., AllinS. M., and SharmaP. K., Synthesis, 1997, 1217.
5.
BennettW.D., In Combinatorial Chemistry; FenniriH., Ed.; Oxford University Press: Oxford, UK, 2000; pp 139–262.
6.
Krchn˘ákV., and HolladayM. W., Chem. Rev., 2002, 102, 61.
7.
(a) GravertD.J., and JandaK. D., Chem. Rev., 1997, 97, 489.
8.
WentworthP., and JandaK. D., Chem. Commun.; 1999, 1917. (c) P.H. Toy and K.D. Tanda, Acc. Chem. Res., 2000, 33, 546.
9.
(a) ZhaoX.-Y., MetzW. A., SieberF., and JandaK. D., Tetrahedron Lett., 1998, 39, 8433.
10.
HarrisJ.M., Poly(ethylene glycol) chemistry: Biotechnical and Biomedical applications; Chap. 1; Plenum Press: New York, 1992.
11.
JohnsonJ. R.Org. React., 1942, 1, 210.
12.
(a) HeckR.F., Org. React., 1982, 27, 345.
13.
HeckR.F., In Comprehensive Organic Synthesis, TrostB., and FlemingI., Eds. Pergamon Press, New York, 1991, Vol. 4, pp. 833.
14.
(a) YuK.-L., DeshpandeM. S., and VyasD. M., Tetrahedron Lett., 1994, 35, 8919. (b) M. Hiroshige, J.R. Hauske and P. Zhou, Tetrahedron Lett., 1995, 36, 4567.
15.
(a) GoffD.A., and ZuckermannR. N., J. Org. Chem., 1995, 60, 5748.
16.
HiroshigeM., HauskeJ. R., and ZhouP., J. Am. Chem. Soc., 1993, 117, 11590.
17.
A mixture of resin 2a and 0.1 N MeONa in MeOH (8 ml) was stirred at r.t. for 3 h. Then Et2O (40 ml) was added. The resulting precipitate was filtered and washed with Et2O. The combined filtrates were washed with Et2O, dried over Na2SO4 and evaporated under reduced pressure to give (E)-methyl cinnamate (4a). 1H NMR: δ = 7.58 (d, J = 15.8 Hz, 1H), 7.11–6.90 (m, 3 H), 6.82–6.71 (m, 2 H), 6.34 (d, J = 15.8 Hz, 1H), 3.75 (s, 3H).
18.
BuckinghamJ., and DonaghyS. M., Dictionary of Organic Compounds; 5th edn. Chapman and Hall, New York, 1983.
19.
WittstruckT.A., and TrachtenbergE. N., J. Am. Chem. Soc., 1967, 89, 3803.
20.
VogelA.I., Textbook of Practical Organic Chemistry; 4th edn. ELBS and Longman, London, 1978.
21.
CaiM.-Z., SongC.-S., and HuangX., Synthesis, 1997, 521.
