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.

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., Shanahan, S. E., Sneddon, H. F., & 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
• Contract Date: Oct 8, 2019