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

Author(s) Chciuk, T.V.; Li, A.M.; Vazquez-Lopez, A.; Anderson, W.R.; Flowers, R.A.
Journal Org Lett
Date Published 2017 Jan 06

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.

DOI 10.1021/acs.orglett.6b03664
ISSN 1523-7052
Citation Org Lett. 2017;19(1):290293.

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