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Deoxygenative Nucleophilic Difluoromethylselenylation of Carboxylic Acids and Alcohols with BT-SeCF2H

Deoxygenative Nucleophilic Difluoromethylselenylation of Carboxylic Acids and Alcohols with BT-SeCF2H

Deoxygenative Nucleophilic Difluoromethylselenylation of Carboxylic Acids and Alcohols with BT-SeCF2H
Image Credit: The Authors

M. Tironi, S. Dix, M. N. Hopkinson* – 2021

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.

Title
39. Deoxygenative Nucleophilic Difluoromethylselenylation of Carboxylic Acids and Alcohols with BT-SeCF2H
Author
M. Tironi, S. Dix, M. N. Hopkinson*
Publisher
Royal Society of Chemistry
Date
2021
Identifier
DOI: 10.1039/D1QO01104A
Source(s)
Citation
Org. Chem. Front. 2021, DOI: 10.1039/D1QO01104A.
Type
Text