Synthesis 2018; 50(09): 1783-1795
DOI: 10.1055/s-0037-1609843
short review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Water-Tolerance in Frustrated Lewis Pair Chemistry

School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK   Email: [email protected]   Email: [email protected]
,
School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK   Email: [email protected]   Email: [email protected]
› Author Affiliations
We acknowledge the University of Manchester, the Royal Society of Chemistry (V.F. - Mobility Research grant) and the EPSRC (M.J.I. - grant numbers EP/K03099X/1 and EP/M023346/1) for financial support.
Further Information

Publication History

Received: 30 January 2018

Accepted after revision: 27 February 2018

Publication Date:
29 March 2018 (online)


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 Brønsted 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 Brønsted 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

 
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