Triiodide‐Mediated δ‐Amination of Secondary C−H Bonds |
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| Authors: | Ethan A Wappes Stacy C Fosu Trevor C Chopko Prof?Dr David A Nagib |
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| Affiliation: | 1. http://www.chemistry.osu.edu/faculty/nagib;2. Department of Chemistry and Biochemistry, The Ohio State University, Columbus, OH, USA |
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| 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. |
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| Keywords: | amination C− H functionalization radical chemistry hydrogen atom transfer triiodide |
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