Electrochemical Benzylic C-H Functionalization with Isocyanides

10 November 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


We report the challenging direct carbamoylation or cyanation of benzylic C(sp3)-H bonds with an isocyanide via an electrochemical process giving rise to structures which are encountered in several biologically relevant compounds and drugs. This transformation proceeds in mild conditions without the need of external oxidant and avoids the necessity to start from a prefunctionalized benzylic substrate or the deployment of the cation pool method. Anodic oxidation of the benzylic position and subsequent addition of the isocyanide leads to the formation of a C-C bond and to a nitrilium cation which hydrolysis leads to alpha-aryl acetamide derivatives, while elimination of a t-butyl cation delivers alpha-aryl acetonitrile derivatives.


benzylic oxidation


Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.