CHED 456 |
| The versatility of the Suzuki coupling reaction between aryl boronic acids and aryl halides has made it a popular choice for carbon-carbon band forming reactions given its tolerance toward many functional groups. Here we report on the step-wise Suzuki coupling of a cationic anthraquinone. We have recently showed that Suzuki coupling of 1-chloro-5-(4'-dimethylaminopyridinium)anthraquinone with 1,4-diboronic acid can give the mono-substituted product, 1-(4'-phenylboronic acid)-5-(4''-dimethylaminopyridinium)anthraquinone (PBPAQ), in high yield. The reason for such a high percent of PBPAQ over the bis-substituted product is that the boronic acid of PBPAQ gives up a proton to form a zwitter-ionic compound that precipitates out of solution at room temperature. In this work, we present further couplings using the zwitter-ionic PBPAQ. |
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Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Poster
Division of Chemical Education |