Download PDF
Synfacts 2009(5): 0567-0567  
DOI: 10.1055/s-0029-1216548
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Flow-Through Reaction in Palladium- Supported Microreactors

Contributor(s):Yasuhiro Uozumi, Yoichi M. A. Yamada, Toshihiro Watanabe
A. Gömann, J. A. Deverell, K. F. Munting, R. C. Jones, T. Rodemann, A. J. Canty, J. A. Smith*, R. M. Guijt*
University of Tasmania, Hobart, Australia
Palladium-Mediated Organic Synthesis Using Porous Polymer Monolith Formed in situ as a Continuous Catalyst Support Structure for Application in Microfluidic Devices
Tetrahedron  2009,  65:  1450-1454  
CrossrefGoogle Scholar
Further Information

Publication History

Publication Date:
22 April 2009 (online)

 PDF Download Permissions and Reprints

Key words

microreactor - microflow reactor - flow-through reactor

Significance

The authors reported the Sonogashira and the Suzuki-Miyaura reaction performed with microflow reactors filled with palladium polymer (Æ 250 µm, length 5 cm). Thus, the Sonogashira reaction of iodobenzene (1a) and phenylacetylene (2) was carried out with the microreactor A or B to give diphenylacetylene (3) in 96% (with A) or 95% yield (with B), respectively. The Suzuki-Miyaura ­reaction of aryl halides 1a-e with 4-tolylboronic acid (4) gave the corresponding biphenyls 5a-e ­under similar flow-reaction conditions in 11-97% yield.

Comment

Chloromethylstyrene (6) and divinyl­benzene (7) were polymerized inside a capillary ­[pretreated with 3-(trimethoxysilyl)propyl meth-acrylate] in the presence of a porogen (toluene-dodecanol) and AIBN to afford a polymer-installed capillary 8. The capillary 8 was subsequently treated with the ligand precursor [1-methylimidazole 9 (for A) or 5-amino-1,10-phenanthroline 10 (for B)] and PdCl2(MeCN)2 to give the reactive capillary A and B.

   Permissions and Reprints