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Halogenated Heterocycles pp 185–218Cite as

Recent Progress on the Halogen Dance Reaction on Heterocycles

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

Abstract

The decoration of heterocycles with functional groups and substituents is of great importance for many fields of chemistry. In this context, selective functionalizations of certain positions in a given heterocyclic system are highly desirable and sought after. One way to achieve such selectivity is the prefunctionalization of defined positions with halides, which can then be further transformed to other functional groups and substituents. Halogen Dance reactions proved to be a valuable tool and it was demonstrated in many cases that positions in heterocyclic systems can be activated for subsequent reactions by selective migration of a halide in the corresponding position, which are otherwise extremely difficult to access. Within this chapter, the progress in halogen dance reactions of the last decade will be discussed. Most reported examples relied on the well-established halogen dance induced by organic lithium bases such as LDA or LTMP. However, also several unusual halogen migrations under neutral or even acidic conditions have been reported and will be presented.

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Abbreviations

BCHD:

Base catalyzed halogen dance

Bn:

Benzyl

Boc:

t-Butoxycarbonyl

BuLi:

Butyllithium

DMF:

Dimethylformamide

E+:

Electrophile

HD:

Halogen dance

LDA:

Lithiumdiisopropylamide

LIDAKOR:

Lithium diisopropylamide-potassium tert-butoxide

LTMP:

Lithium-2,2,6,6-tetramethylpiperidine

LTMP:

Lithiumtetramethylpiperidide

NBS:

N-Bromosuccinimide

NIS:

N-Iodosuccinimide

PMB:

p-Methoxybenzyl

pv:

Pivaloyl

rt:

Room temperature

TBDMS:

t-Butyl-dimethylsilyl

THF:

Tetrahydrofuran

THP:

Tetrahydropyran

TIPS:

Triisopropylsilyl

TMS:

Trimethylsilyl

TMSCl:

Trimethylsilylchloride

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Authors and Affiliations

  1. Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9-163/OC, Vienna, Austria

    Michael Schnürch

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  1. Michael Schnürch
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Correspondence to Michael Schnürch .

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  1. , Department of Physical and Organic Chemi, "Jozef Stefan" Institute, Jamova 39, Ljubljana, 1000, Slovenia

    Jernej Iskra

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Schnürch, M. (2011). Recent Progress on the Halogen Dance Reaction on Heterocycles. In: Iskra, J. (eds) Halogenated Heterocycles. Topics in Heterocyclic Chemistry, vol 27. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2011_64

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