4.8 Article

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

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ORGANIC LETTERS
卷 19, 期 1, 页码 290-293

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b03664

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  1. Department of Chemistry at Lehigh University
  2. National Science Foundation [CHE 1565741]
  3. Division Of Chemistry
  4. Direct For Mathematical & Physical Scien [1565741] Funding Source: National Science Foundation

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Two secondary amides (N-methylayetamide and 2-pyrrolidinione) 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.

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