Unlocking the Potential of Deep Eutectic Solvents and Ligand-to-Metal Charge Transfer Processes: A Reusable Iron-and-UV-Based System for Sustainable C-C Bond Formation.

Autor: González-Gallardo N; Departamento de Química Orgánica and Instituto de Síntesis Orgánica (ISO), Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080, Alicante, Spain., Cores A; Departamento de Química Orgánica and Instituto de Síntesis Orgánica (ISO), Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080, Alicante, Spain., Marset X; Institute of Electrochemistry, Universidad de Alicante, Apdo. 99, 03080, Alicante, Spain., Guijarro N; Institute of Electrochemistry, Universidad de Alicante, Apdo. 99, 03080, Alicante, Spain., Guillena G; Departamento de Química Orgánica and Instituto de Síntesis Orgánica (ISO), Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080, Alicante, Spain., Ramón DJ; Departamento de Química Orgánica and Instituto de Síntesis Orgánica (ISO), Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080, Alicante, Spain.
Jazyk: angličtina
Zdroj: ChemSusChem [ChemSusChem] 2024 Dec 20; Vol. 17 (24), pp. e202400911. Date of Electronic Publication: 2024 Sep 09.
DOI: 10.1002/cssc.202400911
Abstrakt: Catalytic C-H functionalization has provided new opportunities to access novel organic molecules more sustainably and efficiently. However, these procedures typically rely on precious metals or complex organic catalysts as well as on hazardous solvents or reaction conditions. Herein, a pioneering methodology for direct C-C bond formation enabled by Ligand-to-Metal Charge Transfer (LMCT) and mediated by UV irradiation has been developed using Deep Eutectic Solvents (DESs) as sustainable reaction media. This direct C-H bond functionalization via a radical addition to electrophiles was successfully confirmed over a broad scope of substrates. More importantly, this is the first example of photocatalytic C-C bond formation in DESs. An inexpensive and abundant iron catalyst (FeCl 3 ) was used under air and mild conditions. Different functional groups were well tolerated obtaining promising results that were comparable to those reported in the literature. Additionally, the reaction medium along with the catalyst could be reused for up to 5 consecutive cycles without a significant loss in the reaction outcome. Several green metrics were calculated and compared to those of conventional procedures, revealing the advantages of using DESs.
(© 2024 The Authors. ChemSusChem published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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