An atom-economic and step-economic aromatic cyanoalkylation reaction that employs nitriles as building blocks and proceeds through Csp2-H and Csp3-H bond activation steps mediated by NiIII is presented. In addition to cyanomethylation with MeCN, regioselective α-cyanoalkylation was observed with various nitrile substrates to generate secondary and tertiary nitriles. Importantly, to the best of our knowledge these are the first examples of C-H bond activation reactions occurring at a NiIII center, which may exhibit different reactivity and selectivity profiles than those corresponding to analogous NiII centers. Overall, these studies also provide guiding principles to design catalytic C-H activation and functionalization reactions involving high-valent Ni species.

High-valent organometallic nickel complexes mediated C-H bond activation and bond formation reactions

254th National Meeting (2017)

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