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The Sonogashira Coupling of Polymer-Supported Propargylamine with Aryl Iodides

✍ Scribed by Tuomo Leikoski; Sirkku Kallonen; Jari Yli-Kauhaluoma

Book ID: 102253702
Publisher: John Wiley and Sons
Year: 2010
Tongue: German
Weight: 186 KB
Volume: 93
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200900129

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✦ Synopsis

Abstract

The Sonogashira coupling reaction of polymer‐supported propargylamine (=prop‐2‐yn‐1‐amine) with aryl iodides in the presence of the [Pd(PPh~3~)~2~]Cl~2~/CuI catalyst system produces 3‐arylprop‐1‐yn‐1‐amines smoothly at room temperature (Scheme). When propargylamine is attached on Wang resin through a carbamate linker, the common problems with amino functionality in palladium‐catalyzed couplings are overcome. The arylpropynamines are cleaved from the polymer with CF~3~COOH and converted into chromatographically easily separable acetamides. Our solid‐phase method opens a new pathway toward precursors of pharmacologically interesting arylpropynamines and arylpropanamines.

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