SUMAN DAS SUMAN.DAS@NOTTINGHAM.AC.UK
Research Fellow
2,2-Difluoroethylation of heteroatom nucleophiles via a hypervalent iodine strategy
Das, Suman; McIvor, Charlotte; Greener, Andrew; Suwita, Charlotte; Argent, Stephen; O'Duill, Miriam
Authors
Charlotte McIvor
Andrew Greener
Charlotte Suwita
STEPHEN ARGENT stephen.argent@nottingham.ac.uk
Senior Research Fellow
MIRIAM O'DUILL MIRIAM.ODUILL@NOTTINGHAM.AC.UK
Assistant Professor in Chemistry
Abstract
The 2,2-difluoroethyl group is an important lipophilic hydrogen bond donor in medicinal chemistry, but its incorporation into small molecules is often challenging. Herein, we demonstrate electrophilic 2,2 difluoroethylation of thiol, amine and alcohol nucleophiles with a hypervalent iodine reagent, (2,2-difluoro-ethyl)(aryl)iodonium triflate, via a proposed ligand coupling mechanism. This transformation offers a complementary strategy to existing 2,2-difluoroethylation methods and allows access to a wide range of 2,2-difluoroethylated nucleophiles, including the drugs Captopril, Normorphine and Mefloquine.
Working Paper Type | Working Paper |
---|---|
Deposit Date | Jun 20, 2024 |
Publicly Available Date | Jun 20, 2024 |
Public URL | https://nottingham-repository.worktribe.com/output/36016330 |
Publisher URL | https://chemrxiv.org/engage/chemrxiv/article-details/6667f4a4e7ccf7753a7ce502 |
Files
Das Difluoroethylation ChemRxiv2024
(969 Kb)
PDF
Publisher Licence URL
https://creativecommons.org/licenses/by-nc-nd/4.0/
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