De novo Design of Organic Photocatalysts: Bithiophene Derivatives for the Visible-light Induced C-H Functionalization of Heteroarenes

Bottecchia, C. ; Martín, R. ; Abdiaj, I. ; Crovini, E. ; Alcazar, J. ; Orduna, J. (Universidad de Zaragoza) ; Blesa, M.J. (Universidad de Zaragoza) ; Carrillo, J.R. ; Prieto, P. ; Noël, T.

Resumen: Herein, we report the de novo synthesis and characterization of a series of substituted bithiophene derivatives as novel and inexpensive organic photocatalysts. DFT calculations were used to predict a priori their absorption spectra and redox potentials, which were then confirmed with empirical data. The photocatalytic activity of this novel class of organic photoredox catalyst was demonstrated in two visible-light mediated strategies for the C-H functionalization of heteroarenes. The implementation of these strategies in a continuous-flow photo-microreactor afforded moderate to excellent yields within few minutes of reaction time. Due to their straightforward synthesis, low cost and good photocatalytic properties we believe that the proposed bithiophene derivatives could be employed as a new class of organic photoredox catalysts. (Figure presented.).

Idioma: Inglés

DOI: 10.1002/adsc.201801571

Año: 2019

Publicado en: Advanced Synthesis and Catalysis 361, 5 (2019), 945–950
ISSN: 1615-4150

Factor impacto JCR: 5.851 (2019)

Categ. JCR: CHEMISTRY, ORGANIC rank: 5 / 57 = 0.088 (2019) - Q1 - T1
Categ. JCR: CHEMISTRY, APPLIED rank: 7 / 71 = 0.099 (2019) - Q1 - T1

Factor impacto SCIMAGO: 1.661 - Organic Chemistry (Q1) - Catalysis (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E14-17R
Financiación: info:eu-repo/grantAgreement/EC/H2020/641861/EU/Accelerating photoredox catalysis in continuous-flow systems/Photo4Future

Tipo y forma: Artículo (PostPrint)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)