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Synfacts 2008(4): 0436-0436  
DOI: 10.1055/s-2008-1042773
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Solid-Phase Preparation of Conjugated Aromatic Compounds

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Toshihiro Watanabe
T. Doi, H. Inoue, M. Tokita, J. Watanabe, T. Takahashi*
Tokyo Institute of Technology, Japan
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Publication History

Publication Date:
19 March 2008 (online)

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Significance

The conjugated aromatic compounds 6 were prepared in a combinatorial manner. Thus, various functionalized benzoic acids 2 were loaded on Rink amino SynPhase Lanterns 1, and underwent six types of palladium coupling reactions with aryl iodide 3 to give 4. Compound 4 (R = OTHP) was deprotected and subsequently underwent the palladium-catalyzed carbonylation with iodoanisole 5 (R" = I) to give 6 having a OC(O)C6H4OMe terminus after the final cleavage from the resin support. Palladium-catalyzed carbonylation of 4 (R" = OTf) with methoxyphenol 5 (R" = OH) followed by acidic cleavage afforded conjugated aromatic compounds 6 bearing the C(O)OC6H4OMe terminus in 51-96% purity.