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- Title
Triiodide-Mediated δ-Amination of Secondary C−H Bonds.
- Authors
Wappes, Ethan A.; Fosu, Stacy C.; Chopko, Trevor C.; Nagib, David A.
- Abstract
The Cδ−H amination of unactivated, secondary C−H bonds to form a broad range of functionalized pyrrolidines has been developed by a triiodide (I3−)-mediated strategy. By in situ 1) oxidation of sodium iodide and 2) sequestration of the transiently generated iodine (I2) as I3−, this approach precludes undesired I2-mediated decomposition which can otherwise limit synthetic utility to only weak C(sp3)−H bonds. The mechanism of this triiodide-mediated cyclization of unbiased, secondary C(sp3)−H bonds, by either thermal or photolytic initiation, is supported by NMR and UV/Vis data, as well as intercepted intermediates.
- Subjects
HYDROGEN bonding; AMINATION; PYRROLIDINONES; INTERMEDIATES (Chemistry); VOIGT reaction; RING formation (Chemistry); ORGANIC compounds
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 34, p10128
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201604704