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Redox-neutral organocatalytic Mitsunobu reactions

Beddoe, Rhydian H.; Andrews, Keith G.; Magné, Valentin; Cuthbertson, James D.; Saska, Jan; Shannon-Little, Andrew L.; Shanahan, Stephen E.; Sneddon, Helen F.; Denton, Ross M.

Authors

Rhydian H. Beddoe

Keith G. Andrews

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

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