A Fenton Approach to Aromatic Radical Cations and Diarylmethane Synthesis

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2023 Oct 17

PMID 37847050

Authors

Robert Crowley Iii

Berkley Lujan

Alex Martinez

Roni Manasi

Justin D DeBow

Kevin G M Kou

Affiliations

Soon will be listed here.

Abstract

Manipulating carbon-centered radicals to add to electron-deficient systems is a well-precedented process. By coupling the Fe(II)-mediated Fenton reaction with the Fe(III)-mediated single-electron oxidation of anisolic compounds, we demonstrate how electron-rich carbon-centered radicals can react with electron-rich arenes through a radical-polar cascade pathway. This bioinspired approach produces diarylmethane derivatives from simple unfunctionalized precursors.

References

Colgan A, Proctor R, Gibson D, Chuentragool P, Lahdenpera A, Ermanis K . Hydrogen Atom Transfer Driven Enantioselective Minisci Reaction of Alcohols. Angew Chem Int Ed Engl. 2022; 61(25):e202200266. PMC: 9321721. DOI: 10.1002/anie.202200266. View

Chen H . Why the Reactive Oxygen Species of the Fenton Reaction Switches from Oxoiron(IV) Species to Hydroxyl Radical in Phosphate Buffer Solutions? A Computational Rationale. ACS Omega. 2019; 4(9):14105-14113. PMC: 6714542. DOI: 10.1021/acsomega.9b02023. View

Bian Q, Wu C, Yuan J, Shi Z, Ding T, Huang Y . Iron Nitrate-Mediated Selective Synthesis of 3-Acyl-1,2,4-oxadiazoles from Alkynes and Nitriles: The Dual Roles of Iron Nitrate. J Org Chem. 2020; 85(6):4058-4066. DOI: 10.1021/acs.joc.9b03070. View

Horibe T, Ohmura S, Ishihara K . Structure and Reactivity of Aromatic Radical Cations Generated by FeCl. J Am Chem Soc. 2019; 141(5):1877-1881. DOI: 10.1021/jacs.8b12827. View

Yu J, Pan C . Radical C-H functionalization to construct heterocyclic compounds. Chem Commun (Camb). 2016; 52(11):2220-36. DOI: 10.1039/c5cc08872k. View

Furst M, Gans E, Bock M, Heinrich M . Visible-Light-Induced, Catalyst-Free Radical Arylations of Arenes and Heteroarenes with Aryldiazonium Salts. Chemistry. 2017; 23(61):15312-15315. DOI: 10.1002/chem.201703954. View

Shalit H, Libman A, Pappo D . meso-Tetraphenylporphyrin Iron Chloride Catalyzed Selective Oxidative Cross-Coupling of Phenols. J Am Chem Soc. 2017; 139(38):13404-13413. DOI: 10.1021/jacs.7b05898. View

Riviere C, Pawlus A, Merillon J . Natural stilbenoids: distribution in the plant kingdom and chemotaxonomic interest in Vitaceae. Nat Prod Rep. 2012; 29(11):1317-33. DOI: 10.1039/c2np20049j. View

Chen M, White M . A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis. Science. 2007; 318(5851):783-7. DOI: 10.1126/science.1148597. View

10.

Jamison C, Overman L . Fragment Coupling with Tertiary Radicals Generated by Visible-Light Photocatalysis. Acc Chem Res. 2016; 49(8):1578-86. DOI: 10.1021/acs.accounts.6b00284. View

11.

Pallikonda G, Chakravartya M . Benzylic Phosphates in Friedel-Crafts Reactions with Activated and Unactivated Arenes: Access to Polyarylated Alkanes. J Org Chem. 2016; 81(5):2135-42. DOI: 10.1021/acs.joc.5b02441. View

12.

Boerjan W, Ralph J, Baucher M . Lignin biosynthesis. Annu Rev Plant Biol. 2003; 54:519-46. DOI: 10.1146/annurev.arplant.54.031902.134938. View

13.

Nawrat C, Jamison C, Slutskyy Y, MacMillan D, Overman L . Oxalates as Activating Groups for Alcohols in Visible Light Photoredox Catalysis: Formation of Quaternary Centers by Redox-Neutral Fragment Coupling. J Am Chem Soc. 2015; 137(35):11270-11273. PMC: 4632490. DOI: 10.1021/jacs.5b07678. View

14.

Kepp K . Bioinorganic chemistry of Alzheimer's disease. Chem Rev. 2012; 112(10):5193-239. DOI: 10.1021/cr300009x. View

15.

Qin Q, Xie Y, Floreancig P . Diarylmethane synthesis through ReO-catalyzed bimolecular dehydrative Friedel-Crafts reactions. Chem Sci. 2018; 9(45):8528-8534. PMC: 6251338. DOI: 10.1039/c8sc03570a. View

16.

Wardman P, Candeias L . Fenton chemistry: an introduction. Radiat Res. 1996; 145(5):523-31. View

17.

Wu Y, Guo P, Chen L, Duan W, Yang Z, Wang T . Iron-catalyzed tandem oxidative coupling and acetal hydrolysis reaction to prepare formylated benzothiazoles and isoquinolines. Chem Commun (Camb). 2021; 57(26):3271-3274. DOI: 10.1039/d1cc00621e. View

18.

Huang Z, Jin L, Feng Y, Peng P, Yi H, Lei A . Iron-catalyzed oxidative radical cross-coupling/cyclization between phenols and olefins. Angew Chem Int Ed Engl. 2013; 52(28):7151-5. DOI: 10.1002/anie.201210023. View

19.

Sawicki K, Chang H, Ardehali H . Role of heme in cardiovascular physiology and disease. J Am Heart Assoc. 2015; 4(1):e001138. PMC: 4330050. DOI: 10.1161/JAHA.114.001138. View

20.

Smith J, Harwood S, Baran P . Radical Retrosynthesis. Acc Chem Res. 2018; 51(8):1807-1817. PMC: 6349421. DOI: 10.1021/acs.accounts.8b00209. View