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

TitleSecondary Amides as Hydrogen Atom Transfer Promoters for Reactions of Samarium Diiodide
Publication TypeJournal Article
Year of Publication2017
AuthorsChciuk TV, Li AM, Vazquez-Lopez A, Anderson WR, Flowers, II RA
JournalOrganic Letters
Volume19
Issue1
Start Page290
Pagination3
Date Published12/16
Abstract

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.

URLhttp://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b03664
DOI10.1021/acs.orglett.6b03664