Copper-Mediated Sequential Cyanation of Aryl C-B and Arene C-H Bonds Using Ammonium Iodide and DMF was written by Kim, Jinho;Choi, Jiho;Shin, Kwangmin;Chang, Sukbok. And the article was included in Journal of the American Chemical Society in 2012.Quality Control of 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane This article mentions the following:
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, resp. 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. In the experiment, the researchers used many compounds, for example, 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4Quality Control of 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane).
2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Quality Control of 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem