Issue 21, 2021

Deoxygenative nucleophilic difluoromethylselenylation of carboxylic acids and alcohols with BT-SeCF2H

Abstract

The benzothiazolium salt BT-SeCF2H is introduced as an efficient nucleophilic reagent for transferring difluoromethylselenyl groups onto organic molecules. SeCF2H-Containing selenoesters could be prepared upon deoxygenative substitution of readily available carboxylic acids, while silver catalysis allowed for efficient formation of (difluoromethyl)selenoethers, including the established electrophilic reagent BnSeCF2H, directly from simple alcohols. To the best of our knowledge, these deoxygenative reactions represent the first reported nucleophilic difluoromethylselenylation processes and thus open up new approaches to prepare valuable fluorinated compounds.

Graphical abstract: Deoxygenative nucleophilic difluoromethylselenylation of carboxylic acids and alcohols with BT-SeCF2H

Supplementary files

Article information

Article type
Research Article
Submitted
29 7 2021
Accepted
22 8 2021
First published
25 8 2021
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2021,8, 6026-6031

Deoxygenative nucleophilic difluoromethylselenylation of carboxylic acids and alcohols with BT-SeCF2H

M. Tironi, S. Dix and M. N. Hopkinson, Org. Chem. Front., 2021, 8, 6026 DOI: 10.1039/D1QO01104A

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