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Synthesis of Phenyl- and Pyridyl-substituted Benzyloxybenzaldehydes by Suzuki-Miyaura Coupling Reactions

[ Vol. 16 , Issue. 11 ]

Author(s):

Hedvig Bölcskei*, Andrea Német-Hanzelik, Zsófia Dubrovay, Viktor Háda and György Keglevich   Pages 1248 - 1257 ( 10 )

Abstract:


Background: Aryl-methoxybenzaldehydes substituted in various positions may serve as valuable starting materials for the synthesis of biologically active compounds.

Methods: Biaryl-methoxybenzaldehydes and pyridyl-aryl-methoxybenzaldehydes were synthesized by the Suzuki-Miyaura cross-coupling reactions as intermediates of potential drug substances. Three different catalytic approaches were compared. The classical Suzuki method utilising tetrakis(triphenylphosphine)palladium and sodium ethoxide, the protocol applying palladium acetate and tri(o-tolyl)phosphine, and the method using tetrakis(triphenylphosphine)palladium and cesium carbonate, were studied.

Results: The selected boronic acids were the classical phenylboronic acid, as well as 4-pyridineand 3-pyridineboronic acids. 26 New biaryl-methoxybenzaldehydes or pyridyl-phenylmethoxybenzaldehydes have been synthesized, which may be intermediates for pharmaceutically active compounds.

Conclusion: The method of Anderson et al. was preferred, because it provides satisfactory results in all cases.

Keywords:

Suzuki-miyaura cross-coupling reaction, biaryl-oxyaryl-aldehyde, phenylboronic acid, pyridineboronic acids, tetrakis(triphenylphosphine)palladium, palladium acetate.

Affiliation:

Gedeon Richter Plc. Budapest X., Gyomroi ut 30-32, Budapest 10. Pf.27. H-1475, Gedeon Richter Plc. Budapest X., Gyomroi ut 30-32, Budapest 10. Pf.27. H-1475, Gedeon Richter Plc. Budapest X., Gyomroi ut 30-32, Budapest 10. Pf.27. H-1475, Gedeon Richter Plc. Budapest X., Gyomroi ut 30-32, Budapest 10. Pf.27. H-1475, Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1521Budapest

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