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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DOI: https://doi.org/10.1007/7081_2011_62
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