Titel
Hydride Shuttle Catalysis: From Conventional to Inverse Mode
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Abstract
Hydride shuttle catalysis has emerged as a powerful synthetic platform, enabling the selective formation of C–C bonds to yield sp3-rich structures. By virtue of the compelling reactivity of sterically encumbered Lewis acids from the frustrated Lewis pair regime, hydride shuttle catalysis enables the regioselective functionalization of alkyl amines at either the α- or β-position. In contrast to classical Lewis acid reactivity, the increased steric hindrance prevents interaction with the Lewis basic amine itself, instead leading to reversible abstraction of a hydride from the amine α-carbon. The created positive charge facilitates the occurrence of transformations before hydride rebound or a similar capture event happen. In this Perspective, we outline a broad selection of transformations featuring hydride shuttle catalysis, as well as the recently developed approach of inverse hydride shuttle catalysis. Both strategies give rise to a wide array of functionalized amines and offer elegant approaches to otherwise elusive bond formations.
Stichwort
hydride shuttle catalysisborane catalysisfrustrated Lewis pairs
Objekt-Typ
Sprache
Englisch [eng]
Persistent identifier
phaidra.univie.ac.at/o:2095204
Erschienen in
Titel
JACS Au
Band
4
Ausgabe
9
ISSN
2691-3704
Erscheinungsdatum
2024
Seitenanfang
3358
Seitenende
3369
Publication
American Chemical Society (ACS)
Erscheinungsdatum
2024
Zugänglichkeit
Rechteangabe
© 2024 The Authors

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