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Preparation of difluoromethylthioethers through difluoromethylation of disulfides using TMS-CF2H

Howard, JL; Schotten, C; Alston, ST; Browne, DL; (2016) Preparation of difluoromethylthioethers through difluoromethylation of disulfides using TMS-CF2H. Chemical Communications , 52 (54) pp. 8448-8451. 10.1039/c6cc02693a. Green open access

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Abstract

We report an operationally simple, metal-free approach for the late-stage introduction of the important lipophilic hydrogen-bond donor motif, SCF2H. This reaction converts diaryl- and dialkyl-disulfides into the corresponding aryl/alkyl–SCF2H through the nucleophilic transfer of a difluoromethyl group with good functional group tolerance. This method is notable for its use of commercially available TMSCF2H, and does not rely on the need for handling of sensitive metal complexes.

Type: Article
Title: Preparation of difluoromethylthioethers through difluoromethylation of disulfides using TMS-CF2H
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/c6cc02693a
Publisher version: http://dx.doi.org/10.1039/c6cc02693a
Language: English
Additional information: This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Keywords: MEDICINAL CHEMISTRY, CARBONYL-COMPOUNDS, FLUORINE, THIOETHERS, ARYL, TRIMETHYLSILANE, PHARMACEUTICALS, REAGENT, DESIGN, DRUG
UCL classification: UCL
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy
UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharma and Bio Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10114352
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