Secondary Amides as Hydrogen Atom Transfer Promoters for Reactions of Samarium Diiodide

Abstract

Two secondary amides ( N -methylacetamide and 2-pyrrolidinone) were used as additives with SmI 2 in THF to estimate the extent of N–H bond weakening upon coordination. Mechanistic and synthetic studies demonstrate significant bond-weakening, providing a reagent system capable of reducing a range of substrates through formal hydrogen atom transfer.