A microwave irradiated palladium-catalyzed reaction of carboxylic acids and crotyl type bromides creates series of esters in good to high yields. This facile ester synthesis then is applied to make esters from arachidonic acid, salicylic acid, folic acid, and aspirin efficiently.
References
[1]
Marshall, J.A. (2000) Synthesis and Reactions of Allylic, Allenic, Vinylic, and Arylmetal Reagents from Halides and Esters via Transient Organopalladium Intermediates. Chemical Reviews, 100, 3163-3185. https://doi.org/10.1021/cr000003u
[2]
Negishi, E., Huang, Z., Wang, G., Mohan, S., Wang, C. and Hattori, H. (2008) Recent Advances in Efficient and Selective Synthesis of Di-, Tri-, and Tetrasubstituted Alkenes via Pd-Catalyzed Alkenylation-Carbonyl Olefination Synergy. Accounts of Chemical Research, 41, 1474-1485. https://doi.org/10.1021/ar800038e
[3]
Okamoto, N., Miwa, Y., Minami, H., Takeda, K. and Yanada, R. (2011) Regio- and Stereoselective Multisubstituted Enol Ester Synthesis. The Journal of Organic Chemistry, 76, 9133-9138. https://doi.org/10.1021/ar800038e
[4]
Satchell, D.P.N. (1963) An Outline of Acylation. Quarterly Reviews, Chemical Society, 17, 160. https://doi.org/10.1039/qr9631700160
[5]
Eftekhari-Sis, B. and Zirak, M. (2017) α-Imino Esters in Organic Synthesis: Recent Advances. Chemical Reviews, 117, 8326-8419. https://doi.org/10.1021/acs.chemrev.7b00064
[6]
Inanaga, J., Kirata, K., Saeki, H., Katsuki, T. and Yamaguchi, M. (1979) A Rapis Esterification by Means of Mixed Anhydride and Its Application to Large-Ring Lactonization. Bulletin of the Chemical Society of Japan, 52, 1989-1993. https://doi.org/10.1246/bcsj.52.1989
[7]
Fischer, E. (1895) Darstellung der Ester. Berichte der Deutschen Chemischen Gesellschaft, 28, 3252-3258. https://doi.org/10.1002/cber.189502803176
[8]
Grasa, G.A. and Colacot, T.J. (2007) α-Arylation of Ketones Using Highly Active, Air-Stable (DtBPF)PdX2 (X = Cl, Br) Catalysts. Organic Letters, 9, 5489-5492.
[9]
Al-Masum, M., Saleh, N. and Islam, T. (2013) A Novel Route to Organonitrites by Pd-Catalyzed Cross-Coupling of Sodium Nitriteand Potassium Organotri-fluoroborates. Tetrahedron Letters, 54, 1141-1144.
[10]
Mann, G., Shelby, Q., Roy, A.H. and Hartwig, J.F. (2003) Electronic and Steric Effects on the Reductive Elimination of Diaryl Ethers from Palladium(II). Organometallics, 22, 2775-2789. https://doi.org/10.1021/om030230x
[11]
Elsagir, A.R., Gassner, F., Gorls, H. and Dinjus, E. (2000) Bidentate Ferrocenyl Phosphines and Their Palladium(II)Dichloride Complexes—X-Ray Structural and NMR Spectroscopic Investigations and First Results of Their Characteristics in the Pd-Catalyzed Oligomerization of 1,3-Butadiene with CO2. Journal of Organometallic Chemistry, 597, 139-145. https://doi.org/10.1016/S0022-328X(99)00670-1
[12]
Bianchini, C., Meli, A., Overhauser, W., Parisel, S., Passaglia, E., Ciardelli, F., Gusev, O.V., Kal’sin, A.M. and Vologdin, N.V. (2005) Ethylene Carbonylation in Methanol and in Aqueous Media by Palladium(II) Catalysts Modified with 1,1’- Bis(Dialkylphosphino)Ferrocenes. Organometallics, 24, 1018-1030. https://doi.org/10.1021/om049109w
[13]
Martin, S.A., Brash, A.R. and Murphy, R.C. (2016) The Discovery and Early Structural Studies of Arachidonic Acid. The Journal of Lipid Research, 57, 1126-1132. https://doi.org/10.1194/jlr.R068072
[14]
Li, D., Ng, A., Mann, N.J. and Sinclair, A.J. (1998) Contribution of Meat Fat to Dietary Arachidonic Acid. Lipids, 33, 437-440. https://doi.org/10.1007/s11745-998-0225-7
[15]
Tallima, H. and Rashika, E.R. (2018) Arachidonic Acid: Physiological Roles and Potential Health Benefits—A Review. Journal of Advanced Research, 4, 467-468. https://doi.org/10.1016/j.jare.2017.11.004
[16]
Groehn, V., Moser, R. and Pugin, B. (2005) Stereoselective Hydrogenation of Folic Acid Dimethyl Ester Benzenesulfonate: A New Access to Optically Pure l-Tetrahydrofolic Acid. Advanced Synthesis & Catalysis, 347, 1855-1862. https://doi.org/10.1002/adsc.200505098
[17]
Bailey, L.B. (1995) Folate in Health and Disease. Vol. 1, Marcel Dekker, Inc., New York, Basel, Hong Kong, 23-42.
