Organophotoredox assisted cyanation of bromoarenes via silyl-radical-mediated bromine abstraction was written by Shee, Maniklal;Shah, Sk. Sheriff;Singh, N. D. Pradeep. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020.Electric Literature of C12H16BBrO2 This article mentions the following:
The insertion of a nitrile (-CN) group into arenes through the direct functionalization of the C(sp2)-Br bond is a challenging reaction. Herein, we report an organophotoredox method for the cyanation of aryl bromides using the organic photoredox catalyst 4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene) and tosyl cyanide (TsCN) as the nitrile source. A photogenerated silyl radical, via a single electron transfer (SET) mechanism, was employed to abstract bromine from aryl bromide to provide an aryl radical, which was concomitantly intercepted by TsCN to afford the aromatic nitrile. A range of substrates containing electron-donating and -withdrawing groups was demonstrated to undergo cyanation at room temperature in good yields. Thus, e.g., Me 4-bromobenzoate → Me 4-cyanobenzoate (71%) employing 4CzIPN, TsCN, (TMS)3SiOH as silyl radical source, K3PO4 as base, acetone as solvent and irradiation from blue LED. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Electric Literature of C12H16BBrO2).
2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. Tertiary alcohols cannot be oxidized at all without breaking carbon-carbon bonds, whereas primary alcohols can be oxidized to aldehydes or further oxidized to carboxylic acids.Electric Literature of C12H16BBrO2
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts