4.8 Article

Direct C-H Cyanation of Arenes via Organic Photoredox Catalysis

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 8, Pages 2880-2883

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b12708

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Funding

  1. National Institutes of Health (NIGMS) [R01 GM120186]
  2. Eli Lilly Grantee Award

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Methods for the direct C-H functionalization of aromatic compounds are in demand for a variety of applications, including the synthesis of agrochemicals, pharmaceuticals, and materials. Herein, we disclose the construction of aromatic nitriles via direct C-H functionalization using an acridinium photoredox catalyst and trimethylsilyl cyanide under an aerobic atmosphere. The reaction proceeds at room temperature under mild conditions and has proven to be compatible with a variety of electron-donating and -withdrawing groups, halogens, and nitrogen- and oxygen-containing heterocycles, as well as aromatic-containing pharmaceutical agents.

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