Beilstein J. Org. Chem.2018,14, 1039–1045, doi:10.3762/bjoc.14.91
congruence with the reductive iodonio-Claisen rearrangement (RICR) to show that there may be an underlying mechanism which expands the reasoning behind the previously known C–C bond-forming reaction. By rationalizing the hypervalent iodine’s metal-like properties it was concluded that a transmetallation
-guided electrophilic substitution (HIGES).
Keywords: electrophilic aromatic substitution; hypernucleofugality; hypervalent iodine; iodonio-Claisen; transmetallation; Introduction
Hypervalent iodine compounds have been known for over a hundred years, but it was not until their renaissance in the 1990’s
hypervalent iodine-guided electrophilic substitution (HIGES) reaction was discovered. The new reaction is thought to have some similarities to the reductive iodonio-Claisen rearrangement except that, with respect to the iodine, para-substituted instead of ortho-substituted products are mainly isolated. Future
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Graphical Abstract
Scheme 1:
Examples of the reductive iodonio-Claisen rearrangement compared to new reactivity seen with benzyl...