Author, as appears in the article.: Mestre J; Bernús M; Castillón S; Boutureira O

Department: Química Analítica i Química Orgànica

URV's Author/s: Boutureira Martín, Omar / Castillón Miranda, Sergio

Keywords: Nucleophilic trifluoromethylation sulfur sulfides perfluoroalkylthiolation pentafluoroethylation fluorination methods convenient synthesis boronic acids aryl alkynes

Abstract: The introduction of fluoroalkylthioether groups has attracted the attention of the drug-discovery community given the special physicochemical and pharmacokinetic features they confer to bioactive compounds, yet these are often limited to standard SCF3 and SCF2H moieties. Herein, two saccharin-based electrophilic reagents have been disclosed for the incorporation of uncommon SCF2CF2H and SCF2CF3 motifs. Their reactivity performance, multigram-scale preparation, and divergent derivatization have been thoroughly investigated with a variety of nucleophiles, including natural products and pharmaceuticals.

Thematic Areas: Química Organic chemistry Odontología Medicina ii Medicina i Materiais Interdisciplinar General medicine Farmacia Ensino Engenharias iv Engenharias ii Engenharias i Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Ciências agrárias i Ciência de alimentos Chemistry, organic Biotecnología Astronomia / física

licence for use: https://creativecommons.org/licenses/by/3.0/es/

Author's mail: sergio.castillon@urv.cat omar.boutureira@urv.cat

Author identifier: 0000-0002-0690-7549

Record's date: 2023-02-19

Papper version: info:eu-repo/semantics/publishedVersion

Link to the original source: https://pubs.acs.org/doi/10.1021/acs.joc.2c01038

Licence document URL: http://repositori.urv.cat/ca/proteccio-de-dades/

Papper original source: Journal Of Organic Chemistry. 87 (16): 10791-10806

APA: Mestre J; Bernús M; Castillón S; Boutureira O (2022). Electrophilic Reagents for the Direct Incorporation of Uncommon SCF2CF2H and SCF2CF3 Motifs. Journal Of Organic Chemistry, 87(16), 10791-10806. DOI: 10.1021/acs.joc.2c01038

Article's DOI: 10.1021/acs.joc.2c0103810791J

Entity: Universitat Rovira i Virgili

Journal publication year: 2022

Publication Type: Journal Publications