Visible-light-driven 1,2-hydro(cyanomethylation) of alkenes with chloroacetonitrile

A regioselective 1,2-hydro(cyanomethylation) of unactivated aliphatic alkenes is reported. A cyanomethyl radical is generated from haloacetonitriles. This radical adds onto alkenes to form alkyl radicals, which undergo hydrogen atom transfer from thiol to produce one-carbon-extended nitriles. Furthermore, the alkyl radicals are applied to cascade cyclization. One-carbon-extended nitriles are synthesized by a visible-light-driven 1,2-hydro(cyanomethylation) of alkenes with chloroacetonitrile. A cyanomethyl radical adds onto alkenes to form an alkyl radical, which undergoes hydrogen atom transfer from thiol.

Automated summary

This study reports a regioselective approach for the 1,2-hydro(cyanomethylation) of unactivated aliphatic alkenes. A cyanomethyl radical is added onto alkenes to form alkyl radicals, which then undergo further reactions to produce one-carbon-extended nitriles.