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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.

Journal Article Type Article
Journal Chemical Communications
Print ISSN 1359-7345
Electronic ISSN 1364-548X
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 50
APA6 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, doi:10.1039/C4CC02171A
DOI https://doi.org/10.1039/C4CC02171A
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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