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

Research output: Contribution to journalArticle

29 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)9512-9516
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number32
DOIs
Publication statusPublished - Jan 1 2017

Keywords

  • boron
  • frustrated Lewis pairs
  • reductive amination
  • strained molecules
  • water tolerance

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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