Biaryl compounds have become a prominent class of synthetic targets due to their unique structural characteristics. It is these characteristics that allow their use as ligands in metal catalysis, as well as building blocks for natural products. Although selective synthetic methods for constructing biaryls have been reported, opportunities exist for innovative strategies that can broaden the scope of their accessibility. Utilizing a novel Diels-Alder reaction, the synthesis of orthogonally-substituted halogenated biaryls will be presented. Subsequent functionalization using Suzuki couplings, as well as reductions, will be discussed. Specific attention will be paid to meta-substitution relative to the biaryl linkage.
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Back to The 61st Northwest Regional Meeting (June 25 - 28, 2006)