Two secondary amides (N-methylacetamide and 2-pyrrolidinone) were used as additives with SmI 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.
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| http://dx.doi.org/10.1021/acs.orglett.6b03664 | DOI Listing |
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