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

Lookup NU author(s): Dr Matt HopkinsonORCiD

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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.

Publication metadata

Author(s): Tironi M, Dix S, Hopkinson MN

Publication type: Article

Publication status: Published

Journal: Organic Chemistry Frontiers

Year: 2021

Volume: 8

Issue: 21

Pages: 6026-6031

Print publication date: 07/11/2021

Online publication date: 25/08/2021

Acceptance date: 22/08/2021

Date deposited: 16/11/2021

ISSN (electronic): 2052-4129

Publisher: Royal Society of Chemistry

URL: https://doi.org/10.1039/D1QO01104A

DOI: 10.1039/D1QO01104A

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