Summary
The preparation of a new palladium(II) complex with a 2-pyridinealdoxime ligand and its use as a Pd(0) precatalyst in the cross-coupling Suzuki–Miyaura reaction is described. Several concepts for the immobilization of this catalytic system are presented and compared in order to develop an efficient catalytic tool for high-throughput synthesis
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
(a) Miyaura, N. and Suzuki, A., Palladium-catalyzed cross-coupling reactions of organoboron compounds, Chem. Rev., 95 (1995) 2457–2483; (b) Suzuki, A., Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998, J. Organomet. Chem., 576 (1999) 147–168.
Herrmann, W.A., N-Heterocyclic carbenes: A new concept in the organometallic catalysis, Angew. Chem. Int. Ed., 41 (2002) 1290–1309.
(a) Bedford, R.B., Palladacyclic catalysts in C–C and C-heteroatom bond-forming reactions, Chem. Commun. (2003) 1787–1796; (b) Singleton, J.T., The uses of pincer complexes in organic synthesis, Tetrahedron, 59 (2003) 1837–1857.
Alonso, D.A., Nájera, C. and Pacheco, M.C., Oxime palladacycles: Stable and efficient catalysts for carbon–carbon coupling reactions, Org. Lett., 2 (2000) 1823–1826.
(a) Alonso, D.A., Nájera, C. and Pacheco, M.C., Oxime-derived palladium complexes as very efficient catalysts for the Heck-Mizoroki reaction, Adv. Synth. Cat. 344 (2002) 172–183; (b) Alonso, D.A., Nájera, C. and Pacheco, M.C., Highly active oxime-derived palladacycle complexes for Suzuki–Miyaura and Ullmann-Type coupling reactions, J. Org. Chem., 67 (2002) 5588–5594; (c) Alonso, D.A., Nájera, C. and Pacheco, M.C., C(sp2)–C(sp) and C(sp)–C(sp) coupling reactions catalyzed by oxime-derived palladacycles, Adv. Synth. Cat., 345 (2003) 1146–1157.
(a) Frenzel, T., Solodenko, W. and Kirschning, A., Solid-phase bound catalysts – properties and applications, In Buchmeiser, M.R. (Ed.) Polymeric Materials in Organic Synthesis and Catalysis, Wiley-VCH, Weinheim, 2003, pp. 201–240; (b) Clapham, B., Reger, T.S. and Janda, K.D., Polymer-supported catalysis in synthetic organic chemistry, Tetrahedron, 57 (2001) 4637–4661; (c) Gladysz, J.A., Introduction: Recoverable catalysts and reagents – perspective and prospective, Chem. Rev., 102 (2002) 3215–3216; (d) McNamara, C.A., Dixon, M.J. and Bradley, M., Recoverable catalysts and reagents using recyclable polystyrene-based supports, Chem. Rev., 102 (2002) 3275–3299.
Buchmeiser, M.R. and Wurst, K., Access to well-defined heterogeneous catalytic systems via ring-opening metathesis polymerization (ROMP): Application in palladium(II)-mediated coupling reactions, J. Am. Chem. Soc., 121 (1999) 11101–11107.
(a) Baleizao, C., Corma, A., Garcia, H. and Leyva, A., An oxime-carbapalladacycle complex covalently anchored to silica as an active and reusable heterogeneous catalyst for Suzuki cross-coupling in water, Chem. Commun. (2003) 606–607; (b) Baleizao, C., Corma, A., Garcia, H. and Leyva, A., Oxime carbapalladacycle covalently anchored to high surface area inorganic supports or polymers as heterogeneous green catalysts for the Suzuki reaction in water, J. Org. Chem, 69 (2004) 439–446.
Viciu, M.S., Kissling, R.M., Stevens, E.D. and Nolan, S.P., An air-stable palladium/N-heterocyclic carbene complex and its reactivity in aryl animation, Org. Lett., 4 (2002), 2229–2231.
Nájera, C., Gil-Molto, J., Karlstrom, S. and Falvello, L.R., Di-2-pyridylmethylamine-based palladium complexes as new catalysts for Heck, Suzuki, and Sonogashira reactions in organic and aqueous solvents, Org. Lett., 5 (2003) 1451–1454.
(a) Cornils, B. and Herrmann, W.A. (Eds.) Aqueous Organometallic Catalysis, Wiley-VCH, Weinheim, 1998; (b) Anastas, P.T. and Warner, J. (Eds.) Green Chemistry: Theory and Practice, Oxford University Press, New York, 1998.
(a) Herrmann, W.A., Böhm, V.P.W. and Reisinger, C-P., Application of palladacycles in Heck type reactions, J. Organomet. Chem., 576 (1999) 23–41; (b) Nájera, C. and Botella, L., A convenient oxime-carbapalladacycle-catalyzed Suzuki cross-coupling of aryl chlorides in water, Angew. Chem. Int. Ed., 41 (2002) 179–181.
Kunz, U., Schönfeld, H., Kirschning, A. and Solodenko, W., Polymer/carrier composites as materials and reactors for organic synthesis, J. Chromatogr. A, 1006 (2003) 241–249.
(a) Kirschning, A., Altwicker, C., Dräger, G., Harders, J., Hoffmann, N., Hoffmann, U., Schönfeld, H., Solodenko, W. and Kunz, U., PASSflow synthesis using functionalized monolithic polymer/glass composites inflow-through microreactors, Angew. Chem., Int. Ed., 40 (2001) 3995–3998; (b) Solodenko, W., Kunz, U., Jas, G. and Kirschning, A., Polymer-assisted Horner–Emmons olefination using PASSflow reactors: Pure products without purification, Bioorg. Med. Chem. Lett., 12 (2002) 1833–1835.
(a) Austin, R.E., Okonya, J.F., Bond, D.R.S. and Al-Obeidi, F., Microwave-assisted solid-phase synthesis (MASS) of 2,6,9-trisubstituted purines, Tetrahedron Lett., 43 (2002) 6169–6171; (b) Dallinger, D., Gorobets, N.Y. and Kappe, C.O., High-throughput synthesis of N3-acylated dihydropyrimidines combining microwave-assisted synthesis and scavenging techniques, Org. Lett., 5 (2003) 1205–1208.
Yao, Q. and Zhang, Y., Olefin metathesis in the ionic liquid 1-butyl-3-imidazolium hexafluorophosphate using a recyclable Ru catalyst: Remarkable effect of a designer ionic tag, Angew. Chem., 115 (2003) 3517–3520.
(a) Welton, T., Room-temperature ionic liquids. Solvents for synthesis and catalysis, Chem. Rev., 99 (1999) 2071–2083; (b) Wasserscheid, P. and Keim, W., Ionic liquids – New “solutions” for transition metal catalysis, Angew. Chem. Int. Ed., 39 (2000) 3773–3789; (c) Sheldon, R., Catalytic reactions in ionic liquids, Chem. Commun. (2001) 2399–2407.
Mehnert, C.P., Mozeleski, E.J. and Cook, R.A., Supported ionic liquid catalysts investigated for hydrogenation reactions, Chem. Commun. (2002) 3010–3011.
Part of this work was presented at the 8th International Symposium on Solid phase synthesis and combinatorial libraries, Imperial College London, UK, September 2003.
Tulloch, A.D.D., Winston, S., Danopoulos, A.D., Eastman, G. and Hursthouse, M.B., Functionalised and chelate heterocyclic carbene complexes of palladium; synthesis and structural studies, J. Chem. Soc. Dalton Trans. (2003) 699–708.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Solodenko, W., Brochwitz, C., Wartchow, R. et al. 2-Pyridinealdoxime, a new ligand for a Pd-precatalyst: Application in solid-phase-assisted Suzuki–Miyaura reaction. Mol Divers 9, 333–339 (2005). https://doi.org/10.1007/s11030-005-7457-y
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s11030-005-7457-y