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Why do silanes reduce electron-rich phosphine oxides faster than electron-poor phosphine oxides?

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Abstract

Organophosphine-mediated reactions that generate P[double bond, length as m-dash]O-bonded byproducts can be transformed into catalytic processes by reducing the R3P[double bond, length as m-dash]O byproduct back to PR3 in situ with a silane. DFT calculations explain why the most readily reduced phosphine oxides are those incorporating electron-rich (e.g. alkyl) substituents rather than electron-deficient (e.g. aryl) substituents.

Graphical abstract: Why do silanes reduce electron-rich phosphine oxides faster than electron-poor phosphine oxides?

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Article information


Submitted
07 Nov 2019
Accepted
19 Dec 2019
First published
03 Jan 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Why do silanes reduce electron-rich phosphine oxides faster than electron-poor phosphine oxides?

A. M. Kirk, C. J. O’Brien and E. H. Krenske, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC08718D

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