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Triiodide‐Mediated δ‐Amination of Secondary C−H Bonds
Author(s) -
Wappes Ethan A.,
Fosu Stacy C.,
Chopko Trevor C.,
Nagib David A.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201604704
Subject(s) - triiodide , chemistry , amination , iodide , iodine , sodium iodide , medicinal chemistry , photochemistry , combinatorial chemistry , organic chemistry , catalysis , electrolyte , electrode , dye sensitized solar cell
The C δ −H amination of unactivated, secondary C−H bonds to form a broad range of functionalized pyrrolidines has been developed by a triiodide (I 3 − )‐mediated strategy. By in situ 1) oxidation of sodium iodide and 2) sequestration of the transiently generated iodine (I 2 ) as I 3 − , this approach precludes undesired I 2 ‐mediated decomposition which can otherwise limit synthetic utility to only weak C(sp 3 )−H bonds. The mechanism of this triiodide‐mediated cyclization of unbiased, secondary C(sp 3 )−H bonds, by either thermal or photolytic initiation, is supported by NMR and UV/Vis data, as well as intercepted intermediates.