Efficient and Sustainable Laccase-catalyzed Iodination of -substituted Phenols Using KI As Iodine Source and Aerial O As Oxidant

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 May 6

PMID 35519358

Authors

Mark Sdahl

Jurgen Conrad

Christina Braunberger

Uwe Beifuss

Affiliations

Soon will be listed here.

Abstract

The laccase-catalyzed iodination of -hydroxyarylcarbonyl- and -hydroxyarylcarboxylic acid derivatives using KI as iodine source and aerial oxygen as the oxidant delivers the corresponding iodophenols in a highly efficient and sustainable manner with yields up to 93% on a preparative scale under mild reaction conditions.

Citing Articles

Mold resistance of bamboo after laccase-catalyzed attachment of thymol and proposed mechanism of attachment.

Wang J, Wang H, Ye Z, Chizaram E, Jiang J, Liu T RSC Adv. 2022; 10(13):7764-7770.

PMID: 35492150 PMC: 9049941. DOI: 10.1039/d0ra00315h.

Electrochemical synthesis of quinazolinone I-catalyzed tandem oxidation in aqueous solution.

Hou H, Ma X, Lin Y, Lin J, Sun W, Wang L RSC Adv. 2022; 11(29):17721-17726.

PMID: 35480173 PMC: 9033184. DOI: 10.1039/d1ra02706a.

Selective C-H Iodination of (Hetero)arenes.

Tanwar L, Borgel J, Lehmann J, Ritter T Org Lett. 2021; 23(13):5024-5027.

PMID: 34114468 PMC: 8289285. DOI: 10.1021/acs.orglett.1c01530.

References

Cannatelli M, Ragauskas A . Two Decades of Laccases: Advancing Sustainability in the Chemical Industry. Chem Rec. 2016; 17(1):122-140. DOI: 10.1002/tcr.201600033. View

Ihssen J, Schubert M, Thony-Meyer L, Richter M . Laccase catalyzed synthesis of iodinated phenolic compounds with antifungal activity. PLoS One. 2014; 9(3):e89924. PMC: 3940670. DOI: 10.1371/journal.pone.0089924. View

Ross A, Lang H, Jackson R . Much improved conditions for the Negishi cross-coupling of iodoalanine derived zinc reagents with aryl halides. J Org Chem. 2009; 75(1):245-8. DOI: 10.1021/jo902238n. View

Pacardo D, Sethi M, Sharon E Jones , Naik R, Knecht M . Biomimetic synthesis of Pd nanocatalysts for the Stille coupling reaction. ACS Nano. 2009; 3(5):1288-96. DOI: 10.1021/nn9002709. View

Singh C, Prakasham A, Gangwar M, Butcher R, Ghosh P . One-Pot Tandem Hiyama Alkynylation/Cyclizations by Palladium(II) Acyclic Diaminocarbene (ADC) Complexes Yielding Biologically Relevant Benzofuran Scaffolds. ACS Omega. 2019; 3(2):1740-1756. PMC: 6641338. DOI: 10.1021/acsomega.7b01974. View

Hajdok S, Conrad J, Leutbecher H, Strobel S, Schleid T, Beifuss U . The laccase-catalyzed domino reaction between catechols and heterocyclic 1,3-dicarbonyls and the unambiguous structure elucidation of the products by NMR spectroscopy and X-ray crystal structure analysis. J Org Chem. 2009; 74(19):7230-7. DOI: 10.1021/jo9011915. View

Fernandes T, Vaz B, Eberlin M, da Silva A, Costa P . Palladium-catalyzed tandem Heck-lactonization from o-iodophenols and enoates: synthesis of coumarins and the study of the mechanism by electrospray ionization mass spectrometry. J Org Chem. 2010; 75(21):7085-91. DOI: 10.1021/jo1010922. View

Xu F, Shin W, Brown S, Wahleithner J, Sundaram U, Solomon E . A study of a series of recombinant fungal laccases and bilirubin oxidase that exhibit significant differences in redox potential, substrate specificity, and stability. Biochim Biophys Acta. 1996; 1292(2):303-11. DOI: 10.1016/0167-4838(95)00210-3. View

Thorell J, Johansson B . Enzymatic iodination of polypeptides with 125I to high specific activity. Biochim Biophys Acta. 1971; 251(3):363-9. DOI: 10.1016/0005-2795(71)90123-1. View

10.

Johansson Seechurn C, Kitching M, Colacot T, Snieckus V . Palladium-catalyzed cross-coupling: a historical contextual perspective to the 2010 Nobel Prize. Angew Chem Int Ed Engl. 2012; 51(21):5062-85. DOI: 10.1002/anie.201107017. View

11.

Kunamneni A, Camarero S, Garcia-Burgos C, Plou F, Ballesteros A, Alcalde M . Engineering and Applications of fungal laccases for organic synthesis. Microb Cell Fact. 2008; 7:32. PMC: 2613868. DOI: 10.1186/1475-2859-7-32. View

12.

Abdel-Mohsen H, Conrad J, Beifuss U . Laccase-catalyzed domino reaction between catechols and 6-substituted 1,2,3,4-tetrahydro-4-oxo-2-thioxo-5-pyrimidinecarbonitriles for the synthesis of pyrimidobenzothiazole derivatives. J Org Chem. 2013; 78(16):7986-8003. DOI: 10.1021/jo401193e. View

13.

Schnepel C, Sewald N . Enzymatic Halogenation: A Timely Strategy for Regioselective C-H Activation. Chemistry. 2017; 23(50):12064-12086. DOI: 10.1002/chem.201701209. View

14.

Podgorsek A, Zupan M, Iskra J . Oxidative halogenation with "green" oxidants: oxygen and hydrogen peroxide. Angew Chem Int Ed Engl. 2009; 48(45):8424-50. DOI: 10.1002/anie.200901223. View

15.

Jereb M, Zupan M, Stavber S . Effective and selective iodofunctionalisation of organic molecules in water using the iodine-hydrogen peroxide tandem. Chem Commun (Camb). 2004; (22):2614-5. DOI: 10.1039/b409919b. View

16.

Francke R, Schnakenburg G, Waldvogel S . Synthesis of highly fluorinated 2,2'-biphenols and 2,2'-bisanisoles. Org Lett. 2010; 12(19):4288-91. DOI: 10.1021/ol101698a. View

17.

Morozova O, Shumakovich G, Gorbacheva M, Shleev S, Yaropolov A . "Blue" laccases. Biochemistry (Mosc). 2007; 72(10):1136-50. DOI: 10.1134/s0006297907100112. View

18.

Brent G . Mechanisms of thyroid hormone action. J Clin Invest. 2012; 122(9):3035-43. PMC: 3433956. DOI: 10.1172/JCI60047. View

19.

Pommier J, Sokoloff L, Nunez J . Enzymatic iodination of protein. Kinetics of iodine formation and protein iodination catalyzed by horse-radish peroxidase. Eur J Biochem. 1973; 38(3):497-506. DOI: 10.1111/j.1432-1033.1973.tb03085.x. View

20.

Hubbard A, COHN Z . The enzymatic iodination of the red cell membrane. J Cell Biol. 1972; 55(2):390-405. PMC: 2108805. DOI: 10.1083/jcb.55.2.390. View