ORGN 269 |
| The biaryl substructure is a privileged motif in biologically active and functional molecules. Over the last decades, the mild and selective Suzuki coupling of arylboronic acids with aryl halides has become the method of choice for laboratory and industrial applications. However, it suffers from a fundamental drawback: It requires the use of stoichiometric amounts of expensive organometallic compounds. Thus, as part of our research on the different applications of carboxylic acid derivatives as synthetic equivalents of alkyl, acyl or acid halides in new cross-coupling reactions, we adopted a innovative approach to the synthesis of biaryls. We have developed a novel bifunctional catalyst system which efficiently catalyzes both the decarboxylation of aromatic carboxylates and the cross-coupling of the resulting aryl metal species with aryl halides. This allows us to perform a regioselective biaryl synthesis from carboxylic acids and aryl bromides or chlorides.
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Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 PM, Monday, 11 September 2006 Moscone Center -- Room 133, Oral
Division of Organic Chemistry |
