In:
Angewandte Chemie, Wiley, Vol. 128, No. 34 ( 2016-08-16), p. 10128-10132
Abstract:
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.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v128.34
DOI:
10.1002/ange.201604704
Language:
English
Publisher:
Wiley
Publication Date:
2016
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