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

Éva Dorkó; Márk Szabó; Bianka Kótai; Imre Pápai; Attila Domján; Tibor Soós

doi:10.1002/anie.201703591

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

Angew Chem Int Ed Engl. 2017 Aug 1;56(32):9512-9516. doi: 10.1002/anie.201703591. Epub 2017 Jul 5.

Authors

Éva Dorkó¹, Márk Szabó², Bianka Kótai¹, Imre Pápai¹, Attila Domján², Tibor Soós¹

Affiliations

¹ Institute of Organic Chemistry, Hungarian Academy of Sciences, Research Centre for Natural Sciences, Magyar tudósok körútja 2, 1117, Budapest, Hungary.
² NMR Research Laboratory of IC, Hungarian Academy of Sciences, Research Centre for Natural Sciences, Magyar tudósok körútja 2, 1117, Budapest, Hungary.

PMID: 28591474
DOI: 10.1002/anie.201703591

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 chemoselectivity and generality.

Keywords: boron; frustrated Lewis pairs; reductive amination; strained molecules; water tolerance.

Publication types

Research Support, Non-U.S. Gov't