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The Photochemical Activity of a Halogen-Bonded Complex Enables the Microfluidic Light-Driven Alkylation of Phenols.
Cuadros, Sara; Rosso, Cristian; Barison, Giorgia; Costa, Paolo; Kurbasic, Marina; Bonchio, Marcella; Prato, Maurizio; Filippini, Giacomo; Dell'Amico, Luca.
Afiliação
  • Cuadros S; Department of Chemical Sciences, University of Padova, Via Marzolo 1, 35131 Padova, Italy.
  • Rosso C; Department of Chemical and Pharmaceutical Sciences, CENMAT, Center of Excellence for Nanostructured Materials, INSTM UdR, Trieste, University of Trieste, Via Licio Giorgieri 1, 34127 Trieste, Italy.
  • Barison G; Department of Chemical Sciences, University of Padova, Via Marzolo 1, 35131 Padova, Italy.
  • Costa P; Department of Chemical Sciences, University of Padova, Via Marzolo 1, 35131 Padova, Italy.
  • Kurbasic M; Department of Chemical and Pharmaceutical Sciences, CENMAT, Center of Excellence for Nanostructured Materials, INSTM UdR, Trieste, University of Trieste, Via Licio Giorgieri 1, 34127 Trieste, Italy.
  • Bonchio M; Department of Chemical Sciences, University of Padova, Via Marzolo 1, 35131 Padova, Italy.
  • Prato M; INSTM UdR, Instituto per la Tecnologia delle Membrane, ITM-CNR, UoS di Padova, via Marzolo 1, 35131 Padova, Italy.
  • Filippini G; Department of Chemical and Pharmaceutical Sciences, CENMAT, Center of Excellence for Nanostructured Materials, INSTM UdR, Trieste, University of Trieste, Via Licio Giorgieri 1, 34127 Trieste, Italy.
  • Dell'Amico L; Center for Cooperative Research in Biomaterials (CIC biomaGUNE), Basque Research and Technology Alliance (BRTA), Paseo de Miramón 194, 20014 Donostia, San Sebastián, Spain.
Org Lett ; 24(16): 2961-2966, 2022 04 29.
Article em En | MEDLINE | ID: mdl-35437017
ABSTRACT
A mild light-driven protocol for the direct alkylation of phenols is reported. The process is driven by the photochemical activity of a halogen-bonded complex formed upon complexation of the in situ generated electron-rich phenolate anion with the α-iodosulfone. The reaction proceeds rapidly (10 min) under microfluidic conditions, delivering a wide variety of ortho-alkylated products (27 examples, up to 97% yield, >201 regioselectivity, on a gram scale), including densely functionalized bioactive phenol derivatives.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Fenóis / Halogênios Idioma: En Ano de publicação: 2022 Tipo de documento: Article
Texto completo
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Fenóis / Halogênios Idioma: En Ano de publicação: 2022 Tipo de documento: Article