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Issue 55, 2014
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Development of a redox-free Mitsunobu reaction exploiting phosphine oxides as precursors to dioxyphosphoranes

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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

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Article information


Submitted
24 Mar 2014
Accepted
16 May 2014
First published
19 May 2014

Chem. Commun., 2014,50, 7340-7343
Article type
Communication
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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