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  • Copper-mediated sequential cyanation of aryl C-B and arene C-H bonds using ammonium iodide and DMF.

Copper-mediated sequential cyanation of aryl C-B and arene C-H bonds using ammonium iodide and DMF.

Journal of the American Chemical Society (2012-01-28)
Jinho Kim, Jiho Choi, Kwangmin Shin, Sukbok Chang
ABSTRACT

The cyanation of aromatic boronic acids, boronate esters, and borate salts was developed under copper-mediated oxidative conditions using ammonium iodide and DMF as the source of nitrogen and carbon atom of the cyano unit, respectively. The procedure was successfully extended to the cyanation of electron-rich benzenes, and regioselective introduction of a cyano group at the arene C-H bonds was also achieved. The observation that the reaction proceeds via a two-step process, initial iodination and then cyanation, led us to propose that ammonium iodide plays a dual role to provide iodide and nitrogen atom of the cyano moiety.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
trans-2-Phenylvinylboronic acid, 97%
Pricing and availability is not currently available.
Sigma-Aldrich
4-Nitrophenylboronic acid, ≥95.0%
Pricing and availability is not currently available.
Sigma-Aldrich
Ammonium iodide, ACS reagent, ≥99%
Pricing and availability is not currently available.
Sigma-Aldrich
3-Pyridinylboronic acid, ≥95.0%
Pricing and availability is not currently available.