Redox-Neutral Selenium-Catalysed Isomerisation of Para-Hydroxamic Acids into Para-Aminophenols

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2021 Mar 24

PMID 33760338

Citations 4

Authors

Hsiang-Yu Chuang

Manuel Schupp

Ricardo Meyrelles

Boris Maryasin

Nuno Maulide

Affiliations

Soon will be listed here.

Abstract

A selenium-catalysed para-hydroxylation of N-aryl-hydroxamic acids is reported. Mechanistically, the reaction comprises an N-O bond cleavage and consecutive selenium-induced [2,3]-rearrangement to deliver para-hydroxyaniline derivatives. The mechanism is studied through both O-crossover experiments as well as quantum chemical calculations. This redox-neutral transformation provides an unconventional synthetic approach to para-aminophenols.

Citing Articles

Hydroxylation of Substituted Anilides with Metallaphotocatalysis.

Khatri B, Chen L, Xu D, Salter R, Lin R ACS Omega. 2024; 9(18):19982-19991.

PMID: 38737023 PMC: 11079915. DOI: 10.1021/acsomega.3c10008.

Copper-catalyzed [1,3]-nitrogen rearrangement of aryl ketoximes oxidative addition of N-O bond in inverse electron flow.

Suzuki M, Terada M, Nakamura I Chem Sci. 2023; 14(21):5705-5711.

PMID: 37265725 PMC: 10231427. DOI: 10.1039/d3sc00874f.

An Efficient Continuous Flow Synthesis for the Preparation of -Arylhydroxylamines: Via a DMAP-Mediated Hydrogenation Process.

Chen J, Lin X, Xu F, Chai K, Ren M, Yu Z Molecules. 2023; 28(7).

PMID: 37049731 PMC: 10096002. DOI: 10.3390/molecules28072968.

Redox-Neutral Selenium-Catalysed Isomerisation of para-Hydroxamic Acids into para-Aminophenols.

Chuang H, Schupp M, Meyrelles R, Maryasin B, Maulide N Angew Chem Int Ed Engl. 2021; 60(25):13778-13782.

PMID: 33760338 PMC: 8252732. DOI: 10.1002/anie.202100801.

References

Browne D, Niyomura O, Wirth T . Catalytic use of selenium electrophiles in cyclizations. Org Lett. 2007; 9(16):3169-71. DOI: 10.1021/ol071223y. View

Danilewicz J, Kemp J . Absolute configuration by asymmetric synthesis of (+)-1-(4-acetamidophenoxy)-3-(isopropylamino)-propan-z-ol (practolol). J Med Chem. 1973; 16(2):168-9. DOI: 10.1021/jm00260a020. View

Wonner P, Vogel L, Duser M, Gomes L, Kniep F, Mallick B . Carbon-Halogen Bond Activation by Selenium-Based Chalcogen Bonding. Angew Chem Int Ed Engl. 2017; 56(39):12009-12012. PMC: 5638094. DOI: 10.1002/anie.201704816. View

Leftheris K, Goodman M . Synthesis and beta-adrenergic antagonist activity of stereoisomeric practolol and propranolol derivatives. J Med Chem. 1990; 33(1):216-23. DOI: 10.1021/jm00163a036. View

Wonner P, Vogel L, Kniep F, Huber S . Catalytic Carbon-Chlorine Bond Activation by Selenium-Based Chalcogen Bond Donors. Chemistry. 2017; 23(67):16972-16975. PMC: 5725716. DOI: 10.1002/chem.201704502. View

Zhang X, Sun J, Ding Y, Yu L . Dehydration of Aldoximes Using PhSe(O)OH as the Pre-Catalyst in Air. Org Lett. 2015; 17(23):5840-2. DOI: 10.1021/acs.orglett.5b03011. View

Burger M, Rottger S, Loch M, Jones P, Werz D . Pd-Catalyzed Cyanoselenylation of Internal Alkynes: Access to Tetrasubstituted Selenoenol Ethers. Org Lett. 2020; 22(13):5025-5029. DOI: 10.1021/acs.orglett.0c01582. View

Liao L, Guo R, Zhao X . Organoselenium-Catalyzed Regioselective C-H Pyridination of 1,3-Dienes and Alkenes. Angew Chem Int Ed Engl. 2017; 56(12):3201-3205. DOI: 10.1002/anie.201610657. View

Nakamura I, Owada M, Jo T, Terada M . Concerted [1,3]-Rearrangement in Cationic Cobalt-Catalyzed Reaction of O-(Alkoxycarbonyl)-N-arylhydroxylamines. Org Lett. 2017; 19(8):2194-2196. DOI: 10.1021/acs.orglett.7b00700. View

10.

Ortgies S, Depken C, Breder A . Oxidative Allylic Esterification of Alkenes by Cooperative Selenium-Catalysis Using Air as the Sole Oxidant. Org Lett. 2016; 18(12):2856-9. DOI: 10.1021/acs.orglett.6b01130. View

11.

Balkrishna S, Prasad C, Panini P, Detty M, Chopra D, Kumar S . Isoselenazolones as catalysts for the activation of bromine: bromolactonization of alkenoic acids and oxidation of alcohols. J Org Chem. 2012; 77(21):9541-52. DOI: 10.1021/jo301486c. View

12.

Reich H, Hondal R . Why Nature Chose Selenium. ACS Chem Biol. 2016; 11(4):821-41. DOI: 10.1021/acschembio.6b00031. View

13.

Bock A, Forchhammer K, Heider J, Leinfelder W, Sawers G, Veprek B . Selenocysteine: the 21st amino acid. Mol Microbiol. 1991; 5(3):515-20. DOI: 10.1111/j.1365-2958.1991.tb00722.x. View

14.

Steinbrenner H, Speckmann B, Klotz L . Selenoproteins: Antioxidant selenoenzymes and beyond. Arch Biochem Biophys. 2016; 595:113-9. DOI: 10.1016/j.abb.2015.06.024. View

15.

STADTMAN T . Selenocysteine. Annu Rev Biochem. 1996; 65:83-100. DOI: 10.1146/annurev.bi.65.070196.000503. View

16.

Freudendahl D, Santoro S, Shahzad S, Santi C, Wirth T . Green chemistry with selenium reagents: development of efficient catalytic reactions. Angew Chem Int Ed Engl. 2009; 48(45):8409-11. DOI: 10.1002/anie.200903893. View

17.

Jones K, Porzelle A, Hall A, Woodrow M, Tomkinson N . Copper-catalyzed coupling of hydroxylamines with aryl iodides. Org Lett. 2008; 10(5):797-800. DOI: 10.1021/ol7029273. View

18.

Hashimoto Y, Shudo K, Okamoto T . Modification of deoxyribonucleic acid with reductively activated mitomycin C. Structures of modified nucleotides. Chem Pharm Bull (Tokyo). 1983; 31(3):861-9. DOI: 10.1248/cpb.31.861. View

19.

Breder A, Depken C . Light-Driven Single-Electron Transfer Processes as an Enabling Principle in Sulfur and Selenium Multicatalysis. Angew Chem Int Ed Engl. 2019; 58(48):17130-17147. DOI: 10.1002/anie.201812486. View

20.

Chuang H, Schupp M, Meyrelles R, Maryasin B, Maulide N . Redox-Neutral Selenium-Catalysed Isomerisation of para-Hydroxamic Acids into para-Aminophenols. Angew Chem Int Ed Engl. 2021; 60(25):13778-13782. PMC: 8252732. DOI: 10.1002/anie.202100801. View