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

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

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: https://nottingham-repository.worktribe.com/output/728452
• Publisher URL: http://pubs.rsc.org/en/Content/ArticleLanding/2014/CC/c4cc02171a#!divAbstract