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Synfacts 2007(3): 0330-0330  
DOI: 10.1055/s-2007-968225
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Suzuki Coupling Reaction Using Continuous Flow Capillary Microreactor

Contributor(s): Yasuhiro Uozumi, Tsutomu Kimura
K. F. Bolton, A. J. Canty, J. A. Deverell, R. M. Guijt*, E. F. Hilder, T. Rodemann, J. A. Smith*
University of Tasmania, Hobart, Australia
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Publication History

Publication Date:
20 February 2007 (online)

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Significance

Macroporous [poly(glycidylmeth­acrylate)-co-ethylene dimethacrylate] (GMA-co-EDMA) monolith-supported phenanthroline-palladium complex was prepared in the fused silica capillary and used as catalyst in the Suzuki-Miyaura coupling. The ring-opening reaction of the epoxy groups of GMA-co-EDMA 1 with 5-hydroxy-1,10-phenanthroline gave the GMA-co-EDMA-supported phenanthroline ligand 3 (eq. 1). The complexation of the phenanthroline ligand 3 with PdCl2(MeCN)2 gave palladium complex 4. A solution of 4-methylphenylboronic acid (5), aryl halides 6, and Bu4NOMe in toluene and MeOH was passed through the capillary for 18-96 h to give the biaryls 7a and 7b in 68% and 59% yield, respectively (eq. 2).