Wittig Olefination Using Phosphonium Ion-Pair Reagents Incorporating an Endogenous Base

Org Lett. 2021 Feb 19;23(4):1457-1462. doi: 10.1021/acs.orglett.1c00133. Epub 2021 Feb 2.

Abstract

Despite common perception, the use of strong bases in Wittig chemistry is utterly unnecessary: we report a series of novel ion-pair phosphonium carboxylate reagents which are essentially "storable ylides". These reagents are straightforwardly prepared in excellent yields, and their fluxional nature permits clean olefination of a broad range of aldehydes and even hemiacetals.