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Heterocyclic Reagents Containing Nitrogen–Halogen Bond: Recent Applications

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Book cover Halogenated Heterocycles

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

Abstract

Progress in the chemistry of unique and important reactions utilizing halogens on nitrogens embedded in heterocyclic compounds is discussed. N–X heterocyclic reagents can be useful in halogenation, oxidation, substitution, addition reaction, cyclization, and asymmetric reactions. This review focuses on the recent representative reaction patterns in which N–X heterocyclic reagents are used, with emphasis on developments in this area since 2005.

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Abbreviations

BCIH:

Bis(collidine)iodonium hexafluorophosphate

BNP:

1,1′-Binaphthyl-2,2′-diyl hydrogenphosphate

BPIT:

Bis(pyridine)iodonium tetrafluoroborate

CAN:

Cerium(IV)ammonium nitrate

DBDMH:

1,3-Dibromo-5,5-dimethylhydantoin

DBU:

1,8-Diazabicyclo[5.4.0]undec-7-ene

DHP:

3,4-Dihydro-2H-pyran

DIDMH:

1,3-Diiodo-5,5-dimethylhydantoin

DIPEA:

Diisopropylethylamine

DMAP:

4-(N,N-dimethylamino)pyridine

dppm:

1,1-Bis(diphenylphosphino)methane

HDMS:

1,1,1,3,3,3-Hexamethyldisilazane

IBX:

2-Iodoxybenzoic acid

NBS:

N-Bromosuccinimide

NBSac:

N-Bromosaccharin

NCS:

N-Chlorosuccinimide

NCSac:

N-Chlorosaccharin

NFOBS:

N-Fluoro-O-benzenedisulfonimide

NFPY-BF4 :

N-Fluoropyridinium tetrafluoroborate

NFPY-OTf:

N-Fluoropyridinium trifluoromethanesulfonate

NFSI:

N-Fluorobenzenesulfonimide

NIS:

N-Iodosuccinimide

NISac:

N-Iodosaccharin

PMP:

p-Methoxyphenyl

PTSA:

p-Toluenesulfonic acid

Py:

Pyridine

SDS:

Sodium dodecyl sulfate

Selectfluor® :

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

TADDOL:

α,α,α′,α′-Tetraaryl-2,2-dimethyl-1,3-dioxolan-4,5-dimethanol

TBCA:

Tribromoisocyanuric acid

TBDMS:

tert-Butyldimethylsilyl

TCCA:

Trichloroisocyanuric acid

TEMPO:

2,2,6,6-Tetramethyl-piperidyl-1-oxy

TFA:

Trifluoroacetic acid

TICA:

Triiodoisocyanuric acid

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Minakata, S., Takeda, Y., Hayakawa, J. (2011). Heterocyclic Reagents Containing Nitrogen–Halogen Bond: Recent Applications. In: Iskra, J. (eds) Halogenated Heterocycles. Topics in Heterocyclic Chemistry, vol 27. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2011_62

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