Electrochemical Generation of Alkyl Radicals from Boronic Esters for SOMOphilic Alkynylation

A simple and efficient electrochemical strategy for the generation of alkyl radicals from alkylboronic esters has been developed via <i>in situ</i> formation of redox-active tetracoordinated boronate complexes using phenyllithium. This approach enables selective and mild access to primary, secondary, and tertiary alkyl radicals from readily available precursors to generate variously substituted alkynes in good to high yields. Additionally, performing the deboronative SOMOphilic alkynylation under microfluidic conditions improved the reaction efficiency, leading to enhanced kinetics, higher yields, and reduced energy consumption.