Unexpected Hydrated Electron Source for Preparative Visible-Light Driven Photoredox Catalysis
- PMID: 30672694
- DOI: 10.1021/jacs.8b12223
Unexpected Hydrated Electron Source for Preparative Visible-Light Driven Photoredox Catalysis
Abstract
The hydrated electron is experiencing a renaissance as a superreductant in lab-scale reductions driven by light, both for the degradation of recalcitrant pollutants and for challenging chemical reactions. However, examples for its sustainable generation under mild conditions are scarce. By combining a water-soluble Ir catalyst with unique photochemical properties and an inexpensive diode laser as light source, we produce hydrated electrons through a two-photon mechanism previously thought to be unimportant for laboratory applications. Adding cheap sacrificial donors turns our new hydrated electron source into a catalytic cycle operating in pure water over a wide pH range. Not only is that catalytic system capable of detoxifying a chlorinated model compound with turnover numbers of up to 200, but it can also be employed for two novel hydrated electron reactions, namely, the decomposition of quaternary ammonium compounds and the conversion of trifluoromethyl to difluoromethyl groups.
Similar articles
-
Multi-Photon Excitation in Photoredox Catalysis: Concepts, Applications, Methods.Angew Chem Int Ed Engl. 2020 Jun 22;59(26):10266-10284. doi: 10.1002/anie.201915762. Epub 2020 Apr 7. Angew Chem Int Ed Engl. 2020. PMID: 31945241 Review.
-
Materials and Mechanisms of Photo-Assisted Chemical Reactions under Light and Dark Conditions: Can Day-Night Photocatalysis Be Achieved?ChemSusChem. 2018 Mar 9;11(5):809-820. doi: 10.1002/cssc.201702238. Epub 2018 Feb 19. ChemSusChem. 2018. PMID: 29316318 Review.
-
Laboratory-scale photoredox catalysis using hydrated electrons sustainably generated with a single green laser.Chem Sci. 2017 Nov 1;8(11):7510-7520. doi: 10.1039/c7sc03514d. Epub 2017 Sep 12. Chem Sci. 2017. PMID: 29163905 Free PMC article.
-
3-Aminoperylene and ascorbate in aqueous SDS, one green laser flash … and action! Sustainably detoxifying a recalcitrant chloro-organic.Photochem Photobiol Sci. 2017 Nov 8;16(11):1613-1622. doi: 10.1039/c7pp00311k. Photochem Photobiol Sci. 2017. PMID: 28926067
-
Generating hydrated electrons through photoredox catalysis with 9-anthrolate.Phys Chem Chem Phys. 2015 Jun 7;17(21):13829-36. doi: 10.1039/c5cp01711d. Epub 2015 May 1. Phys Chem Chem Phys. 2015. PMID: 25929856
Cited by
-
Electrophotocatalytic hydrogenation of imines and reductive functionalization of aryl halides.Nat Commun. 2024 Jan 22;15(1):655. doi: 10.1038/s41467-024-45015-6. Nat Commun. 2024. PMID: 38253534 Free PMC article.
-
Improved transition metal photosensitizers to drive advances in photocatalysis.Chem Sci. 2023 Nov 24;15(1):77-94. doi: 10.1039/d3sc04580c. eCollection 2023 Dec 20. Chem Sci. 2023. PMID: 38131090 Free PMC article. Review.
-
Shining Fresh Light on Complex Photoredox Mechanisms through Isolation of Intermediate Radical Anions.ACS Catal. 2023 Jun 30;13(14):9392-9403. doi: 10.1021/acscatal.3c02515. eCollection 2023 Jul 21. ACS Catal. 2023. PMID: 37497378 Free PMC article.
-
Theoretical investigation of Aryl/Alkyl halide reduction with hydrated electrons from energy and AIMD aspects.J Mol Model. 2023 Apr 15;29(5):142. doi: 10.1007/s00894-023-05553-0. J Mol Model. 2023. PMID: 37061582
-
Physical Mechanisms of Intermolecular Interactions and Cross-Space Charge Transfer in Two-Photon BDBT-TCNB Co-Crystals.Nanomaterials (Basel). 2022 Aug 11;12(16):2757. doi: 10.3390/nano12162757. Nanomaterials (Basel). 2022. PMID: 36014621 Free PMC article.
Publication types
LinkOut - more resources
Full Text Sources
Other Literature Sources
Miscellaneous