Revealing the metal-like behavior of iodine: an iodide-catalysed radical oxidative alkenylation.

In this work, we have described an alternative alkenylation approach to illustrate the metal-like behaviour of iodine in cross-coupling reactions. Alkenylation could proceed through iodide catalysed radical initiation, radical addition and iodine promoted alkenyl functionality recovery. Catalytic HI elimination similar to the β-hydride elimination of transition metals was realized for the radical alkenylation of sulfonyl hydrazides. Operando IR and cyclic voltammetry experiments were carried out to confirm the crucial role of iodine in the radical alkenylation process.