As suggested by the efficiency of o,o'-disubstituted styrenes and (Z)-β-methyl-styrene, conjugation did not appear necessary for iterative MHAT and coupling. Indeed, only minor changes to conditions (CsHCO3 and MeOH cosolvent, see Table and SI) allowed electron-neutral alkenes to be engaged by the single catalyst system. As is common in MHAT reactions, 8 1,1-disubstituted alkenes performed better than all substitution patterns, whereas monosubstituted alkenes performed the worst. Nevertheless, aryl-and even alkyl iodides were tolerated, as were amides, esters, ketones and even aldehydes, highlighting the chemoselectivity of the cross-coupling. Additionally, the outer-sphere nature of both alkene functionalization steps allowed hindered alkenes to be engaged with reasonable efficiency: a rare feat in cross-coupling methodology.