Rhydian H. Beddoe
Redox-neutral organocatalytic Mitsunobu reactions
Beddoe, Rhydian H.; Andrews, Keith G.; Magn�, Valentin; Cuthbertson, James D.; Saska, Jan; Shannon-Little, Andrew L.; Shanahan, Stephen E.; Sneddon, Helen F.; Denton, Ross M.
Authors
Keith G. Andrews
Valentin Magn�
James D. Cuthbertson
Jan Saska
Andrew L. Shannon-Little
Stephen E. Shanahan
Helen F. Sneddon
ROSS DENTON ROSS.DENTON@NOTTINGHAM.AC.UK
Professor of Organic Chemistry
Abstract
Nucleophilic substitution reactions of alcohols are amongst the most fundamental and strategically important transformations in organic chemistry. For over half a century these reactions have been achieved using stoichiometric, and often hazardous, reagents to activate the otherwise unreactive alcohols. Here we demonstrate that a specially designed phosphine oxide promotes nucleophilic substitution reactions of primary and secondary alcohols within a redox
neutral catalysis manifold that produces water as the sole by-product. The scope of the catalytic coupling process encompasses a range of acidic pronucleophiles that allow stereospecific construction of carbon-oxygen and carbon-nitrogen bonds.
Citation
Beddoe, R. H., Andrews, K. G., Magné, V., Cuthbertson, J. D., Saska, J., Shannon-Little, A. L., …Denton, R. M. (2019). Redox-neutral organocatalytic Mitsunobu reactions. Science, 365(6456), 910-914. https://doi.org/10.1126/science.aax3353
Journal Article Type | Article |
---|---|
Acceptance Date | Jul 9, 2019 |
Online Publication Date | Aug 29, 2019 |
Publication Date | Aug 30, 2019 |
Deposit Date | Oct 8, 2019 |
Publicly Available Date | Mar 1, 2020 |
Journal | Science |
Print ISSN | 0036-8075 |
Electronic ISSN | 1095-9203 |
Publisher | American Association for the Advancement of Science |
Peer Reviewed | Peer Reviewed |
Volume | 365 |
Issue | 6456 |
Pages | 910-914 |
DOI | https://doi.org/10.1126/science.aax3353 |
Keywords | Multidisciplinary |
Public URL | https://nottingham-repository.worktribe.com/output/2781402 |
Publisher URL | https://science.sciencemag.org/content/365/6456/910 |
Files
Ross Denton Redox Organocatalytic Mitsunobu
(1.2 Mb)
PDF
You might also like
In situ silane activation enables catalytic reduction of carboxylic acids
(2022)
Journal Article
A Practical Catalytic Reductive Amination of Carboxylic Acids
(2020)
Journal Article
Synthesis of 18O-labelled alcohols from unlabelled alcohols
(2020)
Journal Article
The catalytic Mitsunobu reaction: a critical analysis of the current state-of-the-art
(2018)
Journal Article
Downloadable Citations
About Repository@Nottingham
Administrator e-mail: digital-library-support@nottingham.ac.uk
This application uses the following open-source libraries:
SheetJS Community Edition
Apache License Version 2.0 (http://www.apache.org/licenses/)
PDF.js
Apache License Version 2.0 (http://www.apache.org/licenses/)
Font Awesome
SIL OFL 1.1 (http://scripts.sil.org/OFL)
MIT License (http://opensource.org/licenses/mit-license.html)
CC BY 3.0 ( http://creativecommons.org/licenses/by/3.0/)
Powered by Worktribe © 2024
Advanced Search