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Visible-Light-Induced Catalytic Selective Halogenation with Photocatalyst

Truong Giang Luu, Yongju Jung, Hee-Kwon Kim

Molecules. 2021 Dec; 26(23): 7380. Published online 2021 Dec 5. doi: 10.3390/molecules26237380

PMCID:: PMC8659127

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Halogenation in Fungi: What Do We Know and What Remains to Be Discovered?

Bastien Cochereau, Laurence Meslet-Cladière, Yves François Pouchus, Olivier Grovel, Catherine Roullier

Molecules. 2022 May; 27(10): 3157. Published online 2022 May 14. doi: 10.3390/molecules27103157

PMCID:: PMC9144378

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Synthetic Access to Aromatic α-Haloketones

Marre Porré, Gianmarco Pisanò, Fady Nahra, Catherine S. J. Cazin

Molecules. 2022 Jun; 27(11): 3583. Published online 2022 Jun 2. doi: 10.3390/molecules27113583

PMCID:: PMC9182500

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Enzymatic halogenation and dehalogenation reactions: pervasive and mechanistically diverse

Vinayak Agarwal, Zachary D. Miles, Jaclyn M. Winter, Alessandra S. Eustáquio, Abrahim A. El Gamal, Bradley S. Moore

Chem Rev. Author manuscript; available in PMC 2017 Aug 30.

Published in final edited form as: Chem Rev. 2017 Apr 26; 117(8): 5619–5674. Published online 2017 Jan 20. doi: 10.1021/acs.chemrev.6b00571

PMCID:: PMC5575885

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Halogenases: a palette of emerging opportunities for synthetic biology–synthetic chemistry and C–H functionalisation

Charlotte Crowe, Samuel Molyneux, Sunil V. Sharma, Ying Zhang, Danai S. Gkotsi, Helen Connaris, Rebecca J. M. Goss

Chem Soc Rev. 2021 Aug 31; 50(17): 9443–9481. Published online 2021 Aug 9. doi: 10.1039/d0cs01551b

PMCID:: PMC8407142

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Tungstate-Catalyzed Biomimetic Oxidative Halogenation of (Hetero)Arene under Mild Condition

Zhuang Ma, Helin Lu, Ke Liao, Zhilong Chen

iScience. 2020 May 22; 23(5): 101072. Published online 2020 Apr 18. doi: 10.1016/j.isci.2020.101072

PMCID:: PMC7201191

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Structural basis for halogenation by iron- and 2-oxo-glutarate-dependent enzyme WelO5

Andrew J. Mitchell, Qin Zhu, Ailiena O. Maggiolo, Nikhil Ananth, Matthew L. Hillwig, Xinyu Liu, Amie K. Boal

Nat Chem Biol. Author manuscript; available in PMC 2017 Apr 13.

Published in final edited form as: Nat Chem Biol. 2016 Aug; 12(8): 636–640. Published online 2016 Jun 27. doi: 10.1038/nchembio.2112

PMCID:: PMC5391150

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A controlled non-radical chlorine activation pathway on hematite photoanodes for efficient oxidative chlorination reactions

Daojian Tang, Lei Wu, Liubo Li, Niankai Fu, Chuncheng Chen, Yuchao Zhang, Jincai Zhao

Chem Sci. 2024 Feb 22; 15(8): 3018–3027. Published online 2024 Jan 16. doi: 10.1039/d3sc06337b

PMCID:: PMC10882502

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Sustainable methane utilization technology via photocatalytic halogenation with alkali halides

Jun Ma, Can Zhu, Keke Mao, Wenbin Jiang, Jingxiang Low, Delong Duan, Huanxin Ju, Dong Liu, Kun Wang, Yijing Zang, Shuangming Chen, Hui Zhang, Zeming Qi, Ran Long, Zhi Liu, Li Song, Yujie Xiong

Nat Commun. 2023; 14: 1410. Published online 2023 Mar 14. doi: 10.1038/s41467-023-36977-0

PMCID:: PMC10014990

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Frontier Molecular Orbital Contributions to Chlorination versus Hydroxylation Selectivity in the Non-Heme Iron Halogenase SyrB2

Martin Srnec, Edward I. Solomon

J Am Chem Soc. Author manuscript; available in PMC 2018 Feb 15.

Published in final edited form as: J Am Chem Soc. 2017 Feb 15; 139(6): 2396–2407. Published online 2017 Feb 2. doi: 10.1021/jacs.6b11995

PMCID:: PMC5310988

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Halogenation Activity of Mammalian Heme Peroxidases

Jürgen Arnhold, Ernst Malle

Antioxidants (Basel) 2022 May; 11(5): 890. Published online 2022 Apr 30. doi: 10.3390/antiox11050890

PMCID:: PMC9138014

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Brønsted Acidic Ionic Liquid Accelerated Halogenation of Organic Compounds with N-Halosuccinimides (NXS)

Dejan Vražič, Marjan Jereb, Kenneth K. Laali, Stojan Stavber

Molecules. 2013 Jan; 18(1): 74–96. Published online 2012 Dec 21. doi: 10.3390/molecules18010074

PMCID:: PMC6269842

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Conversion of Aryl Iodides into Aryliodine(III) Dichlorides by an Oxidative Halogenation Strategy Using 30% Aqueous Hydrogen Peroxide in Fluorinated Alcohol

Ajda Podgoršek, Jernej Iskra

Molecules. 2010 Apr; 15(4): 2857–2871. Published online 2010 Apr 20. doi: 10.3390/molecules15042857

PMCID:: PMC6257259

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Hypochlorous Acid: From Innate Immune Factor and Environmental Toxicant to Chemopreventive Agent Targeting Solar UV-Induced Skin Cancer

Jeremy A. Snell, Jana Jandova, Georg T. Wondrak

Front Oncol. 2022; 12: 887220. Published online 2022 Apr 29. doi: 10.3389/fonc.2022.887220

PMCID:: PMC9106365

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Copper(I)-catalysed site-selective C(sp³)–H bond chlorination of ketones, (E)-enones and alkylbenzenes by dichloramine-T

Jianwen Jin, Yichao Zhao, Sara Helen Kyne, Kaveh Farshadfar, Alireza Ariafard, Philip Wai Hong Chan

Nat Commun. 2021; 12: 4065. Published online 2021 Jul 1. doi: 10.1038/s41467-021-23988-y

PMCID:: PMC8249392

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Understanding and Improving the Activity of Flavin Dependent Halogenases via Random and Targeted Mutagenesis

Mary C. Andorfer, Jared C. Lewis

Annu Rev Biochem. Author manuscript; available in PMC 2018 Jun 22.

Published in final edited form as: Annu Rev Biochem. 2018 Jun 20; 87: 159–185. Published online 2018 Mar 28. doi: 10.1146/annurev-biochem-062917-012042

PMCID:: PMC6013374

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Photoelectrocatalytic C–H halogenation over an oxygen vacancy-rich TiO₂ photoanode

Zhenhua Li, Lan Luo, Min Li, Wangsong Chen, Yuguang Liu, Jiangrong Yang, Si-Min Xu, Hua Zhou, Lina Ma, Ming Xu, Xianggui Kong, Haohong Duan

Nat Commun. 2021; 12: 6698. Published online 2021 Nov 18. doi: 10.1038/s41467-021-26997-z

Correction in:: Nat Commun. 2021; 12: 7352.

PMCID:: PMC8602285

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A Promiscuous Halogenase for the Derivatization of Flavonoids

Dominik Kolling, Marc Stierhof, Constanze Lasch, Maksym Myronovskyi, Andriy Luzhetskyy

Molecules. 2021 Oct; 26(20): 6220. Published online 2021 Oct 14. doi: 10.3390/molecules26206220

PMCID:: PMC8539768

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Biosynthetic Chlorination of the Piperazate Residue in Kutzneride Biosynthesis by KthP

Wei Jiang, John R. Heemstra, Jr., Ry R. Forseth, Christopher S. Neumann, Soraya Manaviazar, Frank C. Schroeder, Karl J. Hale, Christopher T. Walsh

Biochemistry. 2011 Jul 12; 50(27): 6063–6072. Published online 2011 Jun 7. doi: 10.1021/bi200656k

PMCID:: PMC3129693

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Algorithm-aided engineering of aliphatic halogenase WelO5* for the asymmetric late-stage functionalization of soraphens

Johannes Büchler, Sumire Honda Malca, David Patsch, Moritz Voss, Nicholas J. Turner, Uwe T. Bornscheuer, Oliver Allemann, Camille Le Chapelain, Alexandre Lumbroso, Olivier Loiseleur, Rebecca Buller

Nat Commun. 2022; 13: 371. Published online 2022 Jan 18. doi: 10.1038/s41467-022-27999-1

PMCID:: PMC8766452

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Scheme 3

Oxidative chlorination of anisole (1) with the photocatalytic halogenase mimetic system.

Halogenase‐Inspired Oxidative Chlorination Using Flavin Photocatalysis

Angew Chem Int Ed Engl. 2016 Apr 18;55(17):5342-5345.
Scheme 4

Oxidative chlorination mechanism of the silole dianion {[SiC₄Ph₄]²⁻•2[Li⁺]} (3) by cupric chloride (CuCl₂), via single-electron transfer and chlorination on each silicon atom of the silole moiety.

Synthesis of 1,1′-Bis(1-Methyl/Chloro-2,3,4,5-Tetraphenyl-1-Silacyclopentadienyl) [Ph4C4Si(Me/Cl)-(Me/Cl)SiC4Ph4] from Silole Anion [MeSiC4Ph4]−•[Li+ or Na+] and Silole Dianion [SiC4Ph4]2−•2[Li+]; Oxidative Coupling of Silole Anion [MeSiC4Ph4]−•[Li+ or Na+] by Ferrous Chloride (FeCl2) and Oxidative Coupling and Chlorination of Silole Dianion [SiC4Ph4]2−•2[Li+] by Cupric Chloride (CuCl2)

Molecules. 2019 Oct;24(20):3772.
FIGURE 2

Inactivation curves of E. coli PI-7 WT and 5 categories of PI-7 transposon mutants exposed to chlorination in buffer. Best-fit curves for chlorination are reconstructed from the decay phase of inactivation curves. Half-lives derived from decay constants were also calculated from the portion corresponding to decay phase of chlorination in the inactivation curves. (A) Inactivation curves of PI-7 WT and resistant isolates (Class A isolates) exposed to chlorination; (B) Inactivation curves of PI-7 WT and susceptible isolates (Class B isolates) exposed to chlorination; (C) Inactivation curves of PI-7 WT and isolates with enhanced virulence (Class C isolates) exposed to chlorination; (D) Inactivation curves of PI-7 WT and isolates with enhanced oxidative stress response (Class D isolates) exposed to chlorination; (E) Inactivation curves of PI-7 WT and isolates with enhanced motility and siderophore production (Class E) exposed to chlorination.

Elucidating the Role of Virulence Traits in the Survival of Pathogenic E. coli PI-7 Following Disinfection

Front Bioeng Biotechnol. 2020;8:614186.
Fig. 1Proposed mechanism of the photocatalytic oxidative chlorination reaction.

Room temperature C(sp2)–H oxidative chlorination via photoredox catalysis †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc03010j Click here for additional data file.

Chem Sci. 2017 Oct 1;8(10):7009-7013.