Recent Advances in Water-Tolerance in Frustrated Lewis Pair Chemistry

Valerio Fasano, Michael J. Ingleson*

*Corresponding author for this work

Research output: Contribution to journalReview article (Academic Journal)peer-review

14 Citations (Scopus)

Abstract

A water-tolerant frustrated Lewis pair (FLP) combines a sterically encumbered Lewis acid and Lewis base that in synergy are able to activate small molecules even in the presence of water. The main challenge introduced by water comes from its reversible coordination to the Lewis acid which causes a marked increase in the Bronsted acidity of water. Indeed, the oxophilic Lewis acids typically used in FLP chemistry form water adducts whose acidity can be comparable to that of strong Bronsted acids such as HCl, thus they can protonate the Lewis base component of the FLP. Irreversible proton transfer quenches the reactivity of both the Lewis acid and the Lewis base, precluding small molecule activation. This short review discusses the efforts to overcome water-intolerance in FLP systems, a topic that in less than five years has seen significant progress. 1 Introduction 2 Water-Tolerance (or Alcohol-Tolerance) in Carbonyl Reductions 3 Water-Tolerance with Stronger Bases 4 Water-Tolerant Non-Boron-Based Lewis Acids in FLP Chemistry 5 Conclusions.

Original languageEnglish
Article numberss-2018-z0059-sr
Pages (from-to)1783-1795
Number of pages13
JournalSynthesis (Germany)
Volume50
Issue number9
Early online date29 Mar 2018
DOIs
Publication statusPublished - 2 May 2018

Keywords

  • frustrated Lewis pairs
  • Lewis acid
  • Lewis base
  • reduction
  • water-tolerance

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