Proton-Coupled Electron Transfer in the Reduction of Carbonyls by Samarium Diiodide-Water Complexes

J Am Chem Soc. 2016 Jul 20;138(28):8738-41. doi: 10.1021/jacs.6b05879. Epub 2016 Jul 8.

Abstract

Reduction of carbonyls by SmI2 is significantly impacted by the presence of water, but the fundamental step(s) of initial transfer of a formal hydrogen atom from the SmI2-water reagent system to produce an intermediate radical is not fully understood. In this work, we provide evidence consistent with the reduction of carbonyls by SmI2-water proceeding through proton-coupled electron transfer (PCET). Combined rate and computational studies show that a model aldehyde and ketone are likely reduced through an asynchronous PCET, whereas reduction of a representative lactone occurs through a concerted PCET. In the latter case, concerted PCET is likely a consequence of significantly endergonic initial electron transfer.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.