Author, as appears in the article.: Spennacchio, Mauro; Bernus, Miguel; Stanic, Jelena; Mazzarella, Daniele; Colella, Marco; Douglas, James J; Boutureira, Omar; Noel, Timothy
Department: Química Analítica i Química Orgànica
URV's Author/s: Bernús Pérez, Miguel / Boutureira Martín, Omar
Keywords: Alcohols Amines Chemistry Dehydroxytrifluoromethylthiolation Esters Ethers Mild Reagents Sal Side
Abstract: The trifluoromethyl group (CF3) is a key functionality in pharmaceutical and agrochemical development, greatly enhancing the efficacy and properties of resulting compounds. However, attaching the CF(3 )group to heteroatoms such as sulfur, oxygen, and nitrogen poses challenges because of the lack of general synthetic methods and reliance on bespoke reagents. Here, we present a modular flow platform that streamlines the synthesis of heteroatom-CF3 motifs. Our method uses readily available organic precursors in combination with cesium fluoride as the primary fluorine source, facilitating the rapid generation of N-trifluoromethyl(R) [NCF3(R)], SCF3 (trifluoromethylthio), and OCF3 (trifluoromethoxy) anions on demand without reliance on perfluoroalkyl precursor reagents. This strategy offers a more environmentally friendly synthesis of trifluoromethyl(heteroatom)-containing molecules, with the potential for scalability in manufacturing processes facilitated by flow technology.
Thematic Areas: Administração pública e de empresas, ciências contábeis e turismo Antropologia / arqueologia Astronomia / física Biodiversidade Biotecnología Ciência política e relações internacionais Ciências agrárias i Ciências ambientais Ciências biológicas i Ciências biológicas ii Ciências biológicas iii Ciencias humanas Ciencias sociales Direito Economia Educação física Engenharias i Engenharias ii Engenharias iii Engenharias iv Ensino Farmacia General medicine General o multidisciplinar Geociências Geografía History and philosophy of science Interdisciplinar Materiais Medicina i Medicina ii Medicina veterinaria Multidisciplinary Multidisciplinary sciences Planejamento urbano e regional / demografia Psicología Psychology Química Saúde coletiva Zootecnia / recursos pesqueiros
licence for use: https://creativecommons.org/licenses/by/3.0/es/
Author's mail: miguel.bernus@urv.cat miguel.bernus@urv.cat omar.boutureira@urv.cat miguel.bernus@urv.cat
Author identifier: 0000-0003-0302-0720 0000-0003-0302-0720 0000-0002-0768-8309 0000-0003-0302-0720
Record's date: 2024-11-30
Papper version: info:eu-repo/semantics/acceptedVersion
Papper original source: Science. 385 (6712): 991-996
APA: Spennacchio, Mauro; Bernus, Miguel; Stanic, Jelena; Mazzarella, Daniele; Colella, Marco; Douglas, James J; Boutureira, Omar; Noel, Timothy (2024). A unified flow strategy for the preparation and use of trifluoromethyl-heteroatom anions. Science, 385(6712), 991-996. DOI: 10.1126/science.adq2954
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Entity: Universitat Rovira i Virgili
Journal publication year: 2024
Publication Type: Journal Publications
Repositori URV