Expanding the Boundaries of Water‐Tolerant Frustrated Lewis Pair Hydrogenation: Enhanced Back Strain in the Lewis Acid Enables the Reductive Amination of Carbonyls

The development of a boron/nitrogen‐centered frustrated Lewis pair (FLP) with remarkably high water tolerance is presented. As systematic steric tuning of the boron‐based Lewis acid (LA) component revealed, the enhanced back‐strain makes water binding increasingly reversible in the presence of relat...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-08, Vol.56 (32), p.9512-9516
Main Authors: Dorkó, Éva, Szabó, Márk, Kótai, Bianka, Pápai, Imre, Domján, Attila, Soós, Tibor
Format: Article
Language:English
Subjects:
Amination
Boron
Carbonyl compounds
Carbonyls
Catalysis
frustrated Lewis pairs
Hydrogenation
Lewis acid
reductive amination
strained molecules
water tolerance
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Summary:The development of a boron/nitrogen‐centered frustrated Lewis pair (FLP) with remarkably high water tolerance is presented. As systematic steric tuning of the boron‐based Lewis acid (LA) component revealed, the enhanced back‐strain makes water binding increasingly reversible in the presence of relatively strong base. This advance allows the limits of FLP's hydrogenation to be expanded, as demonstrated by the FLP reductive amination of carbonyls. This metal‐free catalytic variant displays a notably broad chemoselectivity and generality. No fear of water: A boron/nitrogen‐centered frustrated Lewis pair (FLP) with remarkably high water tolerance is presented. Systematic steric tuning of the boron‐based Lewis acid component revealed that enhanced back‐strain makes water binding increasingly reversible in the presence of a relatively strong base. The limits of FLP hydrogenation are thus expanded, as demonstrated by the reductive amination of carbonyls.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201703591