Development and Application of Cyanofunctionalization Reactions across Unsaturated Bonds

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The cooperative catalysis by palladium and triphenylborane effects the intramolecular oxycyanation and aminocyanation of alkenes through the cleavage of O-CN bonds and the subsequent insertion of double bonds. The use of 4, 5-bis(diphenylphosphino)-9, 9dimethylxanthene(Xantphos) as a ligand for palladium is essential for allowing the transformation to proceed with high chemo and regioselectivity. Variously substituted dihydrobenzofurans with both a tetrasubstituted carbon and cyano functionality, which are often found in biologically active substances including some pharmaceuticals, are accessed by the newly developed methodology in a highly efficient manner.