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Synthesis of programmable tetra-ortho-substituted biaryl compounds using Diels-Alder cycloadditions/cycloreversions of disubstituted alkynyl stannanes.

Orthogonally functionalized, programmable biaryl templates have been synthesized utilizing aryl acetylenic stannanes and oxygenated dienes in a cycloaddition/cycloreversion strategy. Sequential functionalization of each of the four ortho positions has been demonstrated. Subsequent resolution of a representative anilino phenol has been accomplished. Additionally, a highly active anhydrous, boroxine-based Suzuki coupling protocol has been developed for conversion of unreactive aryl chlorides.