Visible-Light-Driven ?-Aminoalkyl Radical-Mediated C(sp3)-C(sp) Cross-Coupling of Iodoalkanes and Alkynyl Bromides

We herein report a simple protocol for metal-free cross-coupling between unactivated alkyl iodides and terminal alkynyl bromides promoted by visible light. The salient features of this transformation are the utilization of an organic photocatalyst and commercially available tri-n-butylamine as a reductant. This protocol couples a variety of unactivated iodoalkanes containing different functional groups and with a variety of terminal alkynyl bromides under mild reaction conditions to afford the substituted alkynes in good yields.

Automated summary

A metal-free cross-coupling protocol between unactivated alkyl iodides and terminal alkynyl bromides has been developed, utilizing visible light as the promoter. This reaction employs an organic photocatalyst and commercially available tri-n-butylamine as a reductant, allowing for the coupling of various unactivated iodoalkanes with different functional groups and terminal alkynyl bromides to form substituted alkynes under mild reaction conditions.