There is a growing number of mild, versatile hydrofunctionalization reactions of alkenes that are catalyzed by simple iron salts [1]. These reactions have been proposed to involve both metal hydride and radical intermediates, but the interconversions of these highly reactive species are not well understood, particularly under the catalytic conditions. We have turned our attention to a particularly powerful reaction in this class, the iron-catalyzed reductive cross-coupling of alkenes [2,3]. This presentation will describe our experimental and computational efforts to understand the mechanism. In particular, we evaluate the "hydrogen atom transfer" (HAT), electron transfer, and proton transfer steps of its mechanism with attention to the potential for proton-coupled electron transfer (PCET) [4]. In this way, the impact of fundamental studies on PCET mechanisms is further extended in the realm of practical iron-catalyzed organic transformations.<br/><br/>

Mechanistic studies on iron-catalyzed alkene coupling reactions

255th National Meeting (2018)

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