The realization of this plan is summarized in Table using RAE 5 with either olefin 7 or RAE 8 leading to the same product 6 (see SI for the comprehensive optimization). As illustrated by entries 1-8,15 (olefin-RAE coupling) and 9-14 (RAE-RAE coupling), each reaction variant required simple and similar conditions: the Fe(TPP)Cl complex, a base, a reductant and a 1,2dichloromethane/ acetone solvent mixture. The choice of base proved crucial as exemplified in entries 2-3 with CsOAc emerging optimal. Increased yields are observed after a simple degassing (bubbling Ar) of the reaction mixture, although the presence of air is not detrimental (entry 4). Exclusion of acetone led to lower yields presumably due to catalyst insolubility (entry 5). Addition of other Fe-sources such as Fe(acac)3 led to diminished conversion (entry 6) as well. As observed in other MHAT transformations, the use of pre-formed Ruben's silane proved beneficial (entries 7-8). Turning to the RAE-RAE coupling, the optimized conditions above only led to 9% yield of the desired adduct 6 (entry 9). Increasing the Fe-loading to 20% had a measurable positive effect on conversion (entry 10). The most significant improvement emerged when switching the reductant from a silane to Zn metal (entry 11). A slight change in solvent composition to DCE/acetone 7:4 along with KOAc in place of CsOAc led to a further increase in yield (entries 12-13). The inclusion of a weak acid (Et3N•HCl) likely serves to activate Zn(0) and results in a 61% isolated yield of 6 (entry 14). Notably, the final optimized conditions for RAE-RAE coupling cannot be applied to the closely related olefin-RAE coupling (entry 15) and vice versa (entry 9). Nevertheless, both conditions employ a simple combination of commercially available reagents and the same Fe(TPP)Cl catalyst.