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Organophotoredox assisted cyanation of bromoarenes via silyl-radical-mediated bromine abstraction

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Abstract

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 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.

Graphical abstract: Organophotoredox assisted cyanation of bromoarenes via silyl-radical-mediated bromine abstraction

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Article information


Submitted
08 Jan 2020
Accepted
02 Mar 2020
First published
02 Mar 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Organophotoredox assisted cyanation of bromoarenes via silyl-radical-mediated bromine abstraction

M. Shee, Sk. S. Shah and N. D. P. Singh, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC00163E

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