Photoinduced Single Electron Reduction of the 4-O-5 Linkage in Lignin Models for C-P Coupling Catalyzed by Bifunctional N-Heterocyclic Carbenes

Overview

Journal Adv Sci (Weinh)

Specialty Biomedical Engineering

Date 2024 Aug 5

PMID 39099408

Authors

Qiang Liu

Ying-Zheng Ren

Bei-Bei Zhang

Wen-Xin Tang

Zhi-Xiang Wang

Lin He

Xiang-Yu Chen

Affiliations

Soon will be listed here.

Abstract

Catalytic activation of C-O bonds is considered as a powerful strategy for the production of aromatics from lignin. However, due to the high reduction potentials of diaryl ether 4-O-5 linkage models, their single electron reduction remains a daunting challenge. This study presents the blue light-induced bifunctional N-heterocyclic carbene (NHC)-catalyzed one-electron reduction of diaryl ether 4-O-5 linkage models for the synthesis of trivalent phosphines. The H-bond between the newly devised bifunctional NHC and diaryl ethers is responsible for the success of the single electron transfer. Furthermore, this approach demonstrates selective one-electron reduction of unsymmetric diaryl ethers, oligomeric phenylene oxide, and lignin model.

Citing Articles

Photoinduced Single Electron Reduction of the 4-O-5 Linkage in Lignin Models for C-P Coupling Catalyzed by Bifunctional N-Heterocyclic Carbenes.

Liu Q, Ren Y, Zhang B, Tang W, Wang Z, He L Adv Sci (Weinh). 2024; 11(38):e2406095.

PMID: 39099408 PMC: 11481192. DOI: 10.1002/advs.202406095.

References

Chernowsky C, Chmiel A, Wickens Z . Electrochemical Activation of Diverse Conventional Photoredox Catalysts Induces Potent Photoreductant Activity*. Angew Chem Int Ed Engl. 2021; 60(39):21418-21425. PMC: 8440429. DOI: 10.1002/anie.202107169. View

Halder S, Mandal S, Kundu A, Mandal B, Adhikari D . Super-Reducing Behavior of Benzo[]phenothiazine Anion Under Visible-Light Photoredox Condition. J Am Chem Soc. 2023; 145(41):22403-22412. DOI: 10.1021/jacs.3c05787. View

Zhou Q, Zou Y, Lu L, Xiao W . Visible-Light-Induced Organic Photochemical Reactions through Energy-Transfer Pathways. Angew Chem Int Ed Engl. 2018; 58(6):1586-1604. DOI: 10.1002/anie.201803102. View

Schutyser W, Renders T, van den Bosch S, Koelewijn S, Beckham G, Sels B . Chemicals from lignin: an interplay of lignocellulose fractionation, depolymerisation, and upgrading. Chem Soc Rev. 2018; 47(3):852-908. DOI: 10.1039/c7cs00566k. View

Huber G, Iborra S, Corma A . Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering. Chem Rev. 2006; 106(9):4044-98. DOI: 10.1021/cr068360d. View

Sergeev A, Hartwig J . Selective, nickel-catalyzed hydrogenolysis of aryl ethers. Science. 2011; 332(6028):439-43. DOI: 10.1126/science.1200437. View

Widness J, Enny D, McFarlane-Connelly K, Miedenbauer M, Krauss T, Weix D . CdS Quantum Dots as Potent Photoreductants for Organic Chemistry Enabled by Auger Processes. J Am Chem Soc. 2022; 144(27):12229-12246. PMC: 9306379. DOI: 10.1021/jacs.2c03235. View

Barham J, Coulthard G, Emery K, Doni E, Cumine F, Nocera G . KOtBu: A Privileged Reagent for Electron Transfer Reactions?. J Am Chem Soc. 2016; 138(23):7402-10. DOI: 10.1021/jacs.6b03282. View

Tay N, Chen W, Levens A, Pistritto V, Huang Z, Wu Z . F- and F-Arene Deoxyfluorination via Organic Photoredox-Catalysed Polarity-Reversed Nucleophilic Aromatic Substitution. Nat Catal. 2021; 3(9):734-742. PMC: 8009013. DOI: 10.1038/s41929-020-0495-0. View

10.

Villo P, Shatskiy A, Karkas M, Lundberg H . Electrosynthetic C-O Bond Activation in Alcohols and Alcohol Derivatives. Angew Chem Int Ed Engl. 2022; 62(4):e202211952. PMC: 10107720. DOI: 10.1002/anie.202211952. View

11.

Xu J, Cao J, Wu X, Wang H, Yang X, Tang X . Unveiling Extreme Photoreduction Potentials of Donor-Acceptor Cyanoarenes to Access Aryl Radicals from Aryl Chlorides. J Am Chem Soc. 2021; 143(33):13266-13273. DOI: 10.1021/jacs.1c05994. View

12.

Sheng H, Liu Q, Zhang B, Wang Z, Chen X . Visible-Light-Induced N-Heterocyclic Carbene-Catalyzed Single Electron Reduction of Mono-Fluoroarenes. Angew Chem Int Ed Engl. 2023; 62(12):e202218468. DOI: 10.1002/anie.202218468. View

13.

Constantin T, Zanini M, Regni A, Sheikh N, Julia F, Leonori D . Aminoalkyl radicals as halogen-atom transfer agents for activation of alkyl and aryl halides. Science. 2020; 367(6481):1021-1026. DOI: 10.1126/science.aba2419. View

14.

Liu Q, Ren Y, Zhang B, Tang W, Wang Z, He L . Photoinduced Single Electron Reduction of the 4-O-5 Linkage in Lignin Models for C-P Coupling Catalyzed by Bifunctional N-Heterocyclic Carbenes. Adv Sci (Weinh). 2024; 11(38):e2406095. PMC: 11481192. DOI: 10.1002/advs.202406095. View

15.

Shirakawa E, Itoh K, Higashino T, Hayashi T . tert-Butoxide-mediated arylation of benzene with aryl halides in the presence of a catalytic 1,10-phenanthroline derivative. J Am Chem Soc. 2010; 132(44):15537-9. DOI: 10.1021/ja1080822. View

16.

Naumann R, Lehmann F, Goez M . Generating Hydrated Electrons for Chemical Syntheses by Using a Green Light-Emitting Diode (LED). Angew Chem Int Ed Engl. 2017; 57(4):1078-1081. DOI: 10.1002/anie.201711692. View

17.

Sanderson K . Lignocellulose: A chewy problem. Nature. 2011; 474(7352):S12-4. DOI: 10.1038/474S012a. View

18.

Zhang N, Samanta S, Rosen B, Percec V . Single electron transfer in radical ion and radical-mediated organic, materials and polymer synthesis. Chem Rev. 2014; 114(11):5848-958. DOI: 10.1021/cr400689s. View

19.

Schmalzbauer M, Marcon M, Konig B . Excited State Anions in Organic Transformations. Angew Chem Int Ed Engl. 2020; 60(12):6270-6292. PMC: 7986118. DOI: 10.1002/anie.202009288. View

20.

Chmiel A, Williams O, Chernowsky C, Yeung C, Wickens Z . Non-innocent Radical Ion Intermediates in Photoredox Catalysis: Parallel Reduction Modes Enable Coupling of Diverse Aryl Chlorides. J Am Chem Soc. 2021; 143(29):10882-10889. DOI: 10.1021/jacs.1c05988. View