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

Dorkó, Éva and Szabó, Márk and Kótai, Bianka and Pápai, Imre and Domján, Attila and Soós, Tibor (2017) Expanding the Boundary of Water-Tolerant Frustrated Lewis Pair Hydrogenation: Enhanced Back Strain in the Lewis Acid Enables the Reductive Amination of Carbonyls. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 56 (32). pp. 9512-9516. ISSN 1433-7851

Preview

Text FLP_redukamin_rev (2).pdf - Draft Version Download (393kB) | Preview

Abstract

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 chemo-selectivity and generality.

Actions (login required)

Edit Item