Combined Cyanoborylation, C-H Activation Strategy for Styrene Functionalization.

A one-pot multicomponent copper-catalyzed protocol for borylation/ortho-cyanation of styrene derivatives followed by a Suzuki-Miyaura coupling provides a platform to explore the factors that control the selectivity between distal or proximal functionalization of arenes. The development of divergent nitrile-directed C-H functionalization (acetoxylation, pivalation, and methoxylation) offers an effective approach to rapidly increase synthetic complexity. Finally, the development of a mild reductive decyanation allows a traceless method to access functionalized biaryl motifs.