Lewis Acid Mediated Electrophilic Cyanation of 2,2'-Biphenols.

A Lewis acid mediated electrophilic cyanation of 2,2'-biphenols with a trifluoromethanesulfonyl (Tf) protecting group is reported. The cyanation reactions with less toxic, commercially available MeSCN as a cyanating reagent afforded a range of 3-cyan-2,2'-biphenols in moderate to high yields. The use of trifluoromethanesulfonyl (Tf) as a protecting group is crucial to the success of this transformation. Moreover, the cyanated products were readily transformed into various synthetically useful molecules. This protocol features high efficiency, excellent regioselectivity, and good functional group compatibility and may provide a practical tool for the synthesis and modification of biologically active compounds, catalysts, and ligands.