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

Tang, Xiaoping; Chapman, Charlotte; Whiting, Matthew; Denton, Ross Matthew

Authors

Xiaoping Tang

Charlotte Chapman

Matthew Whiting

Ross Matthew Denton



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.

Citation

Tang, X., Chapman, C., Whiting, M., & Denton, R. M. (in press). Development of a redox-free mitsunobu reaction exploiting phosphine oxides as precursors to dioxyphosphoranes. Chemical Communications, 50, https://doi.org/10.1039/C4CC02171A

Journal Article Type Article
Acceptance Date May 16, 2014
Online Publication Date May 19, 2014
Deposit Date Aug 22, 2016
Publicly Available Date Aug 22, 2016
Journal Chemical Communications
Print ISSN 1359-7345
Electronic ISSN 1364-548X
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 50
DOI https://doi.org/10.1039/C4CC02171A
Public URL http://eprints.nottingham.ac.uk/id/eprint/35947
Publisher URL http://pubs.rsc.org/en/Content/ArticleLanding/2014/CC/c4cc02171a#!divAbstract
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingh.../end_user_agreement.pdf

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Chem Comm 2014 for e-prints.pdf (558 Kb)
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Copyright Statement
Copyright information regarding this work can be found at the following address: http://eprints.nottingham.ac.uk/end_user_agreement.pdf





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