Articles producció científica> Química Analítica i Química Orgànica

A unified flow strategy for the preparation and use of trifluoromethyl-heteroatom anions

  • Dades identificatives

    Identificador: imarina:9387497
    Autors:
    Spennacchio, MauroBernus, MiguelStanic, JelenaMazzarella, DanieleColella, MarcoDouglas, James JBoutureira, OmarNoel, Timothy
    Resum:
    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.
  • Altres:

    Autor segons l'article: Spennacchio, Mauro; Bernus, Miguel; Stanic, Jelena; Mazzarella, Daniele; Colella, Marco; Douglas, James J; Boutureira, Omar; Noel, Timothy
    Departament: Química Analítica i Química Orgànica
    Autor/s de la URV: Bernús Pérez, Miguel / Boutureira Martín, Omar
    Paraules clau: Alcohols Amines Chemistry Dehydroxytrifluoromethylthiolation Esters Ethers Mild Reagents Sal Side
    Resum: 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.
    Àrees temàtiques: 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
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    Adreça de correu electrònic de l'autor: miguel.bernus@urv.cat miguel.bernus@urv.cat omar.boutureira@urv.cat miguel.bernus@urv.cat
    Identificador de l'autor: 0000-0003-0302-0720 0000-0003-0302-0720 0000-0002-0768-8309 0000-0003-0302-0720
    Data d'alta del registre: 2024-11-30
    Versió de l'article dipositat: info:eu-repo/semantics/acceptedVersion
    Referència a l'article segons font original: Science. 385 (6712): 991-996
    Referència de l'ítem segons les normes 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
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2024
    Tipus de publicació: Journal Publications
  • Paraules clau:

    History and Philosophy of Science,Multidisciplinary,Multidisciplinary Sciences
    Alcohols
    Amines
    Chemistry
    Dehydroxytrifluoromethylthiolation
    Esters
    Ethers
    Mild
    Reagents
    Sal
    Side
    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
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