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submitted on 05.10.2020 and posted on 06.10.2020by Gabriel M. Kiefl, Tanja Gulder
Reversing the polarity in molecules is a versatile
tool for expanding the boundaries of structural space.
Despite a manifold of different umpolung methods available
today, overcoming the inherent reactivity still remains a
constant challenge in organic chemistry. The oxidative
α-functionalization of ketones by external nucleophiles
constitute such an example. Herein, we present a
hypervalent F-iodane mediated umpolung of pyridyl ketones
triggered by Lewis base Lewis acid non-covalent
interactions. A wide variety of external nucleophiles are
introduced with high regioselectivity applying this substratedirecting concept.