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Expanding the Boundaries of Water‐Tolerant Frustrated Lewis Pair Hydrogenation: Enhanced Back Strain in the Lewis Acid Enables the Reductive Amination of Carbonyls
Author(s) -
Dorkó Éva,
Szabó Márk,
Kótai Bianka,
Pápai Imre,
Domján Attila,
Soós Tibor
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201703591
Subject(s) - frustrated lewis pair , reductive amination , lewis acids and bases , chemoselectivity , chemistry , steric effects , boron , catalysis , ammonia borane , amination , polymer chemistry , combinatorial chemistry , organic chemistry , dehydrogenation
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.