α‑Functionalization of Ketones via a Nitrogen Directed Oxidative Umpolung

α‑Functionalization of Ketones via a Nitrogen Directed Oxidative Umpolung

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...

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Veröffentlicht in:Journal of the American Chemical Society 2020-12, Vol.142 (49), p.20577-20582
Hauptverfasser: Kiefl, Gabriel M, Gulder, Tanja
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creator Kiefl, Gabriel M
Gulder, Tanja
description 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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