Aromatic cyanoalkylation through double c-h activation mediated by Ni(III)

Wen Zhou, Shuai Zheng, Jason W. Schultz, Nigam P. Rath, Liviu M. Mirica

Research output: Contribution to journalArticlepeer-review


Herein we report an atom- and step-economic aromatic cyanoalkylation reaction that employs nitriles as building blocks and proceeds through C2-H and C3-H bond activation steps mediated by NiIII. 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. These studies provide guiding principles to design catalytic C-H activation and functionalization reactions involving high-valent Ni species.

Original languageEnglish (US)
Pages (from-to)5777-5780
Number of pages4
JournalJournal of the American Chemical Society
Issue number18
StatePublished - May 11 2016
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry


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