Secondary Amides as Hydrogen Atom Transfer Promoters for Reactions of Samarium Diiodide.
Tesia V ChciukAnna M LiAndres Vazquez-LopezWilliam R AndersonRobert A FlowersPublished in: Organic letters (2016)
Two secondary amides (N-methylacetamide and 2-pyrrolidinone) were used as additives with SmI2 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.