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Green Methods in Halogenation of Heterocycles

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Halogenated Heterocycles

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 27))

Abstract

This chapter will give an overview on a recent research in direct halogenation of heterocyclic compounds with an aim to present environmentally friendlier methods to the existing ones. First, a brief outline on halogenation strategies that are used in nature will be given to compare the development of man-made halogenation. Major part of the chapter will cover new methods of halogenation of heterocyclic compounds that were reported in recent 5 years and deal with the development of new reactions or transformations of known methods into an environmentally friendlier outfit. Methods were grouped into three sections – electrophilic (molecular halogens, trihalides, N-X reagents, oxidative halogenation, electrochemistry), radical, and nucleophilic halogenation. Each of them was further grouped according to the “green” approach that was studied: solvent-free reaction conditions, alternative solvents (water, ionic liquids), activation (microwaves, ultrasound), or new technologies (microreactors).

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Abbreviations

aq.:

Aqueous

ar:

Aryl

Bn:

Benzyl

BOC:

Butoxycarbonyl

BPO:

Bromoperoxidase

CPO:

Chloroperoxidase

DCM:

Dichloromethane

DMF:

Dimethylformamide

EDC:

Ethylene dichloride

E-factor:

Environmental factor, defined by mass of waste per mass of product

equiv.:

Equivalent

Et:

Ethyl

FEC:

Fluoroethylene carbonate

HetAr:

Heteroaryl

His:

Histidine

HPO:

Haloperoxidase

IL:

Ionic liquid

LDH:

Layered double hydroxide

Me:

Methyl

MW:

Microwaves

NBS:

N-Bromosuccinimide

NCS:

N-Chlorosuccinimide

NFSi:

N-Fluorobenzenesulfonimide

NIS:

N-Iodosuccinimide

NXS:

N-Halosuccinimide

POM:

Polyoxometalate

PV:

Phase-vanishing

rt:

Room temperature

SAM:

S-adenosylmethionine

SDS:

Sodium dodecyl sulfate

Selectfluor™ F-TEDA:

1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

Ser:

Serine

TBAB:

Tetrabutylammonium bromide

TBAF:

Tetrabutylammonium fluoride

TBHP:

tert-Butylhydroperoxide

Tf:

Trifluoromethylsulfonyl

Tyr:

Tyrosine

Us:

Ultrasound

X:

Halogen

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  1. Laboratory of Organic and Bioorganic Chemistry, Department of Physical and Organic Chemistry, “Jožef Stefan” Institute, Jamova 39, 1000, Ljubljana, Slovenia

    Jernej Iskra

  2. Centre of Excellence for Integrated Approaches in Chemistry and Biology of Proteins (CIPKeBiP), Jamova 39, 1000, Ljubljana, Slovenia

    Jernej Iskra

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    Jernej Iskra

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Iskra, J. (2011). Green Methods in Halogenation of Heterocycles. In: Iskra, J. (eds) Halogenated Heterocycles. Topics in Heterocyclic Chemistry, vol 27. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2011_60

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