Cyanation and cyanomethylation of trimethylammonium salts via electrochemical cleavage of C-N bonds

We have developed a practical and mild electrochemical protocol for cyanation and cyanomethylation of trimethylammonium salts through a pathway involving C-N bond cleavage without the need for an external stoichiometric reducing agent or a sacrificial anode. The reaction employs tosyl cyanide (TsCN) or azido allyl alcohol as the cyanation or cyanomethylation reagent, respectively. It shows high functional group compatibility and can be applied for the cyanation of natural product derivatives. Preliminary mechanistic studies indicate the involvement of a radical addition pathway.

Automated summary

A practical and mild electrochemical protocol has been developed for cyanation and cyanomethylation of trimethylammonium salts through C-N bond cleavage without the need for external stoichiometric reducing agents or sacrificial anodes. The reaction shows high functional group compatibility and can be used for the synthesis of natural product derivatives. Preliminary mechanistic studies suggest the involvement of a radical addition pathway.