achieved through such methods. The cross coupling between two different redox active esters has also been reported but is not generally applicable to quaternary center synthesis. Here we show how a single catalyst can mediate regioselective quaternization of carbon using ubiquitous chemical feedstocks: olefins and carboxylic acids (Figure ). An inexpensive Fe-based catalyst in the presence of simple reducing agents can effectively achieve this powerful transformation in a chemoselective fashion with broad substrate scope through a similar mechanistic pathway. It is particularly striking that a single catalyst can both activate distinct functional groups (RAEs and olefins) and mediate bond formation between them. An illustrative demonstration of the power of such a reaction is depicted in Figure wherein the 10-step synthesis of a seemingly trivial structure (4) 10 can be truncated into a single step by coupling a primary tosylate-containing RAE 3 with either RAE 1 or olefin 2 with high chemoselectivity in 47% and 42% yield, respectively.