Abstract
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 noncovalent interactions. A wide variety of external nucleophiles are introduced with high regioselectivity applying this substrate-directing concept.
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