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.
Recent Advances in Water-Tolerance in Frustrated Lewis Pair Chemistry / V. Fasano, M.J. Ingleson. - In: SYNTHESIS. - ISSN 0039-7881. - 50:9(2018 May), pp. ss-2018-z0059-sr.1783-ss-2018-z0059-sr.1795. [10.1055/s-0037-1609843]
Recent Advances in Water-Tolerance in Frustrated Lewis Pair Chemistry
V. FasanoPrimo
;
2018
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.File | Dimensione | Formato | |
---|---|---|---|
s-0037-1609843.pdf
accesso riservato
Tipologia:
Publisher's version/PDF
Dimensione
467.08 kB
Formato
Adobe PDF
|
467.08 kB | Adobe PDF | Visualizza/Apri Richiedi una copia |
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.