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Hypervalent Iodine‐Mediated Aziridination of Alkenes: Mechanistic Insights and Requirements for Catalysis
Author(s) -
Richardson Robert D.,
Desaize Magalie,
Wirth Thomas
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200700306
Subject(s) - hypervalent molecule , reagent , chemistry , alkene , catalysis , iodine , reaction mechanism , combinatorial chemistry , organic chemistry , reaction conditions
By detailed study of the possible side reactions in the previously reported aziridination of alkenes with N ‐aminoheterocycles mediated by hypervalent iodine reagents, the requirements to make this reaction catalytic in iodoarene have been determined. The reaction requires an oxidant that will oxidise iodoarenes but that does not oxidise alkenes, but it is possible that no such oxidant actually exists! A method in which the hypervalent iodine reagent can be recycled without the need for reisolation is possible. Further study into the mechanism of this reaction gives tentative evidence that the reaction proceeds through formation of an aminoiodane that reacts directly with the alkene, contrary to previous literature reports in which an acetoxyamine intermediate is suggested. The temperature effect of this reaction is remarkable.