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

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• 作者：Tesia V. Chciuk ; Anna M. Li ; Andres Vazquez-Lopez ; William R. Anderson Jr. ; Robert A. Flowers II
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：January 6, 2017
• 年：2017
• 卷：19
• 期：1
• 页码：290-293
• 全文大小：285K
• ISSN：1523-7052

文摘

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.