Issue 55, 2014

Development of a redox-free Mitsunobu reaction exploiting phosphine oxides as precursors to dioxyphosphoranes

Abstract

The development of the first redox-free protocol for the Mitsunobu reaction is described. This has been achieved by exploiting triphenylphosphine oxide – the unwanted by-product in the conventional Mitsunobu reaction – as the precursor to the active P(V) coupling reagent. Multinuclear NMR studies are consistent with hydroxyl activation via an alkoxyphosphonium salt.

Graphical abstract: Development of a redox-free Mitsunobu reaction exploiting phosphine oxides as precursors to dioxyphosphoranes

Supplementary files

Article information

Article type
Communication
Submitted
24 Mar 2014
Accepted
16 May 2014
First published
19 May 2014

Chem. Commun., 2014,50, 7340-7343

Author version available

Development of a redox-free Mitsunobu reaction exploiting phosphine oxides as precursors to dioxyphosphoranes

X. Tang, C. Chapman, M. Whiting and R. Denton, Chem. Commun., 2014, 50, 7340 DOI: 10.1039/C4CC02171A

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