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2000
Volume 29, Issue 12
  • ISSN: 1385-2728
  • E-ISSN: 1875-5348

Abstract

N-Chlorosuccinimide (NCS) is a five-membered N-containing heterocyclic molecule. This is a versatile reagent and is successfully employed for different types of reactions. Initially, this was employed for chlorination only but soon became an excellent reagent for many reactions, including halocyclizations, functional group transformations, formation of carbon-carbon bonds, This review article covers representative applications of NCS for aliphatic and aromatic chlorination, chlorination of atoms other than carbon, oxidation, and other reactions.

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References

  1. ChauhanP. N-Chlorosuccinimide (NCS).Synlett2010201081285128610.1055/s‑0029‑1219581
     [Google Scholar]
  2. TscherniacJ. Knowledge of chlorimides.Ber. Dtsch. Chem. Ges.19013434209421410.1002/cber.190103403152
     [Google Scholar]
  3. ZimmerH. AudriethL.F. Tertiary butyl hypochlorite as as N-chlorinating agent.J. Am. Chem. Soc.195476143856385710.1021/ja01643a082
     [Google Scholar]
  4. VirgilS.C. N-Chlorosuccinimide.Encyclopedia of Reagents for Organic SynthesisJohn Wiley & SonsNew York.19951768773
     [Google Scholar]
  5. BrethericL. Handbook of Reactive Chemical Hazards.5th edLondonButterworth-Heinemann1995
     [Google Scholar]
  6. FieserM. FieserL.F. Reagents for organic synthesis.John Wiley & Sons1974
     [Google Scholar]
  7. GołebiewskiW. GucmaM. Applications of N-chlorosuccinimide in organic synthesis.Synthesis20072007233599361910.1055/s‑2007‑990871
     [Google Scholar]
  8. KimK.S. ChoI.H. YooB.K. SongY.H. HahnC.S. Selective oxidation of primary and secondary alcohols using di-isopropyl sulphide–N-chlorosuccinimide.J. Chem. Soc. Chem. Commun.1984121276276310.1039/C39840000762
     [Google Scholar]
  9. KohlH.H. WheatleyW.B. WorleyS.D. BodorN. Antimicrobial activity of N-chloramine compounds.J. Pharm. Sci.198069111292129510.1002/jps.26006911167005422
     [Google Scholar]
  10. JuengeE.C. SpanglerP.L. DuncanW.P. The reaction of 1,3,5-Trichloro-2,4,6-trioxo-hexahydro-s-triazine with tetrahydrofuran and related cyclic ethers.J. Org. Chem.196631113836383810.1021/jo01349a503
     [Google Scholar]
  11. SinghZ. KaurJ. KaurR. HundalS.S. Toxic effects of organochlorine pesticides: A review.Am. J. Biomed. Sci.2016411
     [Google Scholar]
  12. LeeJ.C. BaeY.H. ChangS.K. Efficient alpha-halogenation of carbonyl compounds by N-bromosuccinimide and N-chlorosuccinimde.Bull. Korean Chem. Soc.200324440740810.5012/bkcs.2003.24.4.407
     [Google Scholar]
  13. MeshramH.M. ReddyP.N. SadashivK. YadavJ.S. Amberlyst-15®-promoted efficient 2-halogenation of 1,3-keto-esters and cyclic ketones using N-halosuccinimides.Tetrahedron Lett.200546462362610.1016/j.tetlet.2004.11.140
     [Google Scholar]
  14. Mellegaard-WaetzigS.R. WangC. TungeJ.A. Selenium-catalyzed oxidative halogenation.Tetrahedron200662307191719810.1016/j.tet.2005.12.072
     [Google Scholar]
  15. LeyS.V. WhittleA.J. A convenient preparation of 2-haloenones from enones using phenylselenium halides.Tetrahedron Lett.198122343301330410.1016/S0040‑4039(01)81890‑6
     [Google Scholar]
  16. MurphyM. LynchD. SchaefferM. KissaneM. ChopraJ. O’BrienE. FordA. FergusonG. MaguireA.R. Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of α-thioamides to α-thio-β-chloroacrylamides.Org. Biomol. Chem.2007581228124110.1039/B618540A17406721
     [Google Scholar]
  17. MeiY. BentleyP.A. DuJ. Thiourea catalysis of NCS in the synthesis of α-chloroketones.Tetrahedron Lett.200849233802380410.1016/j.tetlet.2008.03.154
     [Google Scholar]
  18. WittkoppA. SchreinerP.R. Metal-free, noncovalent catalysis of diels-alder reactions by neutral hydrogen bond donors in organic solvents and in water.Chemistry20039240741410.1002/chem.20039004212532289
     [Google Scholar]
  19. SchreinerP.R. WittkoppA. H-bonding additives act like Lewis acid catalysts.Org. Lett.20024221722010.1021/ol017117s11796054
     [Google Scholar]
  20. OkinoT. HoashiY. TakemotoY. Thiourea-catalyzed nucleophilic addition of TMSCN and ketene silyl acetals to nitrones and aldehydes.Tetrahedron Lett.200344142817282110.1016/S0040‑4039(03)00433‑7
     [Google Scholar]
  21. SohtomeY. TanataniA. HashimotoY. NagasawaK. Development of novel chiral urea catalysts for the hetero-Michael reaction.Chem. Pharm. Bull.200452447748010.1248/cpb.52.47715056971
     [Google Scholar]
  22. MaherD.J. ConnonS.J. Acceleration of the DABCO-promoted Baylis–Hillman reaction using a recoverable H-bonding organocatalyst.Tetrahedron Lett.20044561301130510.1016/j.tetlet.2003.11.062
     [Google Scholar]
  23. MencheD. HassfeldJ. LiJ. MencheG. RitterA. RudolphS. Hydrogen bond catalyzed direct reductive amination of ketones.Org. Lett.20068474174410.1021/ol053001a16468756
     [Google Scholar]
  24. HoashiY. OkinoT. TakemotoY. Enantioselective Michael addition to α,β-unsaturated imides catalyzed by a bifunctional organocatalyst.Angew. Chem. Int. Ed.200544264032403510.1002/anie.20050045915906403
     [Google Scholar]
  25. VeenemanG.H. van LeeuwenS.H. van BoomJ.H. Iodonium ion promoted reactions at the anomeric centre. II An efficient thioglycoside mediated approach toward the formation of 1,2-trans linked glycosides and glycosidic esters.Tetrahedron Lett.19903191331133410.1016/S0040‑4039(00)88799‑7
     [Google Scholar]
  26. BentleyP.A. MeiY. DuJ. Thiourea catalysis of NCS in the synthesis of β-chloroethers.Tetrahedron Lett.200849162653265510.1016/j.tetlet.2008.02.040
     [Google Scholar]
  27. PravstI. ZupanM. StavberS. Halogenation of ketones with N-halosuccinimides under solvent-free reaction conditions.Tetrahedron200864225191519910.1016/j.tet.2008.03.048
     [Google Scholar]
  28. ZhengZ. HanB. WuF. ShiT. LiuJ. ZhangY. HaoJ. One-step for the preparation of α-haloacetal of ketones with N-bromosuccinimide/N-chlorosuccinimide (NBS/NCS) and ethylene glycol.Tetrahedron201672487738774310.1016/j.tet.2016.05.064
     [Google Scholar]
  29. KeZ. LamY.P. ChanK.S. YeungY.Y. Zwitterion-catalyzed deacylative dihalogenation of β-oxo amides.Org. Lett.202022187353735710.1021/acs.orglett.0c0270132870014
     [Google Scholar]
  30. LebarillierL. OuturquinF. PaulmierC. Synthesis and reactivity of α- and β-Chloro-α-phenylselanyl Esters.Tetrahedron200056387495750210.1016/S0040‑4020(00)00648‑7
     [Google Scholar]
  31. BernardiL. JørgensenK.A. Enantioselective chlorination and fluorination of β-keto phosphonates catalyzed by chiral Lewis acids.Chem. Commun.200510101324132610.1039/B415568H15742066
     [Google Scholar]
  32. ZhaoM.X. ZhangZ.W. ChenM.X. TangW.H. ShiM. Cinchona alkaloid catalyzed enantioselective chlorination of 3‐aryloxindoles.Eur. J. Org. Chem.20112011163001300810.1002/ejoc.201100061
     [Google Scholar]
  33. LiuK.C. SheltonB.R. HoweR.K. A particularly convenient preparation of benzohydroximinoyl chlorides (nitrile oxide precursors).J. Org. Chem.198045193916391810.1021/jo01307a039
     [Google Scholar]
  34. FoleyD.A. DoeckeC.W. BuserJ.Y. MerrittJ.M. MurphyL. KissaneM. CollinsS.G. MaguireA.R. KaernerA. ReactNMR and ReactIR as reaction monitoring and mechanistic elucidation tools: The NCS mediated cascade reaction of α-thioamides to α-thio-β-chloroacrylamides.J. Org. Chem.201176239630964010.1021/jo201212p22029382
     [Google Scholar]
  35. SchwarzL. GirreserU. ClementB. Synthesis and characterization of para‐substituted N, N′‐dihydroxybenzamidines and their derivatives as model compounds for a class of prodrugs.Eur. J. Org. Chem.2014201491961197510.1002/ejoc.201301622
     [Google Scholar]
  36. WingardL.A. GuzmánP.E. SabatiniJ.J. A chlorine gas-free synthesis of dichloroglyoxime.Org. Process Res. Dev.20162091686168810.1021/acs.oprd.6b00252
     [Google Scholar]
  37. Hernández-CalvaA. Meléndez-BalbuenaL. Arroyo-CarranzaM. Ramírez-MonroyA. Halogenation of aldoximes. A versatile reaction for the synthesis of highly functionalized hydroximoyl chlorides and furazan N-oxides.Russ. J. Org. Chem.202359122221222910.1134/S1070428023120217
     [Google Scholar]
  38. YamaneT. MitsuderaH. ShundohT. A new approach to the synthesis of 2-aryl-4-halomethyl-5-methyl-1, 3-oxazoles by highly regioselective direct halogenation with NBS or NCS/MeCN.Synthesis20042004172825283210.1055/s‑2004‑834862
     [Google Scholar]
  39. YamaneT. MitsuderaH. ShundohT. Highly regioselective direct halogenation: A simple and efficient method for preparing 4-halomethyl-5-methyl-2-aryl-1,3-thiazoles.Tetrahedron Lett.2004451697310.1016/j.tetlet.2003.10.113
     [Google Scholar]
  40. JacobsJ. VanT.N. StevensC.V. MarkusseP. De CoomanP. MaatL. De KimpeN. 1,4-Dehydrochlorination of 1-(1-haloalkyl)-3,4-dihydroisoquinolines as a convenient route to functionalized isoquinolines.Tetrahedron Lett.200950263698370110.1016/j.tetlet.2009.03.211
     [Google Scholar]
  41. LiuX. WangY. ChenS. JiaQ. WangG. LiS. Direct benzylic polychlorination of (poly)azines with N -chlorosuccinimide.Org. Chem. Front.202310133336334010.1039/D3QO00611E
     [Google Scholar]
  42. YoshimitsuT. FukumotoN. TanakaT. Enantiocontrolled synthesis of polychlorinated hydrocarbon motifs: A nucleophilic multiple chlorination process revisited.J. Org. Chem.200974269670210.1021/jo802093d19053592
     [Google Scholar]
  43. PimentaL.S. GusevskayaE.V. AlbertoE.E. Intermolecular halogenation/esterification of alkenes with N ‐halosuccinimide and acetic acid catalyzed by 1,4‐diazabicyclo[2.2.2]octane.Adv. Synth. Catal.2017359132297230310.1002/adsc.201700117
     [Google Scholar]
  44. BentleyP.A. MeiY. DuJ. Thiourea catalysis of NCS in the synthesis of chlorohydrins.Tetrahedron Lett.20084981425142710.1016/j.tetlet.2007.11.211
     [Google Scholar]
  45. MurrayR.E. A high yield procedure for 1-chloro-1-alkynes.Synth. Commun.198010534534910.1080/00397918008061822
     [Google Scholar]
  46. BucosM. Villalonga-BarberC. Micha-ScrettasM. SteeleB.R. ScrettasC.G. HeropoulosG.A. Microwave assisted solid additive effects in simple dry chlorination reactions with N-chlorosuccinimide.Tetrahedron201066112061206510.1016/j.tet.2010.01.033
     [Google Scholar]
  47. LiZ.H. FiserB. JiangB.L. LiJ.W. XuB.H. ZhangS.J. N -Hydroxyphthalimide/benzoquinone-catalyzed chlorination of hydrocarbon C–H bond using N -chlorosuccinimide.Org. Biomol. Chem.201917133403340810.1039/C9OB00216B30869109
     [Google Scholar]
  48. XiangM. ZhouC. YangX.L. ChenB. TungC.H. WuL.Z. Visible light-catalyzed benzylic C–H bond chlorination by a combination of organic dye (Acr+-Mes) and N-chlorosuccinimide.J. Org. Chem.202085149080908710.1021/acs.joc.0c0100032434320
     [Google Scholar]
  49. WeinzierlD. PiringerM. ZebrowskiP. StockhammerL. WaserM. Photochemical wolff rearrangement initiated generation and subsequent α-chlorination of C1 ammonium enolates.Org. Lett.202325173126313010.1021/acs.orglett.3c0098637098273
     [Google Scholar]
  50. LiaoS. LiangJ. LiC. ChenN. YangK. ChenJ. SongQ. Synthesis of α-haloboronates by the halogenation of gem-diborylalkanes via tetracoordinate boron species.Org. Lett.202325162928293310.1021/acs.orglett.3c0098237071548
     [Google Scholar]
  51. XingR.G. LiY.N. ZhangB.W. Preparation of chloro-functionalized reduced graphene oxide by silver-catalyzed radical reaction.Chin. Chem. Lett.201728240741110.1016/j.cclet.2016.10.017
     [Google Scholar]
  52. ZhangY. ShibatomiK. YamamotoH. Lewis acid catalyzed highly selective halogenation of aromatic compounds.Synlett20051828372842
     [Google Scholar]
  53. DuB. JiangX. SunP. Palladium-catalyzed highly selective ortho-halogenation (I, Br, Cl) of arylnitriles via sp2 C-H bond activation using cyano as directing group.J. Org. Chem.20137862786279110.1021/jo302765g23373558
     [Google Scholar]
  54. KalyaniD. DickA.R. AnaniW.Q. SanfordM.S. A simple catalytic method for the regioselective halogenation of arenes.Org. Lett.20068122523252610.1021/ol060747f16737304
     [Google Scholar]
  55. LiJ.T. WangL.X. WangD.X. ZhaoL. WangM.X. Synthesis, resolution, structure, and racemization of inherently chiral 1,3-alternate azacalix[4]pyrimidines: Quantification of conformation mobility.J. Org. Chem.20147952178218810.1021/jo500054v24512534
     [Google Scholar]
  56. LiB. LiuB. ShiB.F. Copper-catalyzed ortho-halogenation of arenes and heteroarenes directed by a removable auxiliary.Chem. Commun.201551245093509610.1039/C5CC00531K25712552
     [Google Scholar]
  57. SamantaR.C. YamamotoH. Selective halogenation using an aniline catalyst.Chemistry20152134119761197910.1002/chem.20150223426185028
     [Google Scholar]
  58. MaddoxS.M. NalbandianC.J. SmithD.E. GustafsonJ.L. A practical Lewis base catalyzed electrophilic chlorination of arenes and heterocycles.Org. Lett.20151741042104510.1021/acs.orglett.5b0018625671756
     [Google Scholar]
  59. BovonsombatP. SophanpanichkulP. PandeyA. TungsirisurpS. LimthavornlitP. ChobtumskulK. KuhataparukP. SathityatiwatS. TeecomegaetP. Novel regioselective aromatic chlorination via catalytic thiourea activation of N-chlorosuccinimide.Tetrahedron Lett.201556172193219610.1016/j.tetlet.2015.03.034
     [Google Scholar]
  60. MoghaddamF.M. TavakoliG. SaeedniaB. LangerP. JafariB. Palladium-catalyzed carbamate-directed regioselective halogenation: A route to halogenated anilines.J. Org. Chem.20168193868387610.1021/acs.joc.6b0032927072283
     [Google Scholar]
  61. HeringT. KönigB. Photocatalytic activation of N-chloro compounds for the chlorination of arenes.Tetrahedron201672487821782510.1016/j.tet.2016.06.028
     [Google Scholar]
  62. TangR.J. MilcentT. CrousseB. Regioselective halogenation of arenes and heterocycles in hexafluoroisopropanol.J. Org. Chem.201883293093810.1021/acs.joc.7b0292029256248
     [Google Scholar]
  63. RogersD.A. GallegosJ.M. HopkinsM.D. LignieresA.A. PitzelA.K. LamarA.A. Visible-light photocatalytic activation of N-chlorosuccinimide by organic dyes for the chlorination of arenes and heteroarenes.Tetrahedron2019753613049810.1016/j.tet.2019.130498
     [Google Scholar]
  64. IvanovaY.B. ChizhovaN.V. ShumilovaI.A. RusanovA.I. MamardashviliN.Z. Acid–base properties of polyhalogenated tetraphenylporphyrins.Russ. J. Org. Chem.20205661054106110.1134/S1070428020060147
     [Google Scholar]
  65. MatsuokaJ. YanoY. HiroseY. MashibaK. SawadaN. NakamuraA. MaegawaT. Elemental sulfur-mediated aromatic halogenation.J. Org. Chem.202489177077710.1021/acs.joc.3c0225938113515
     [Google Scholar]
  66. XuJ. LiX. LiQ. TianW. YangX. Dabco-catalysed selective chlorination of aromatics.Tetrahedron Lett.202413615492810.1016/j.tetlet.2024.154928
     [Google Scholar]
  67. StroganovaT.A. VasilinV.K. ShitikovN.V. DmitrievaI.G. KrapivinG.D. 3-Aminofuro[2,3-b]pyridines: Reaction with N-chlorosuccinimide and sodium hypochlorite.Russ. J. Gen. Chem.202494231432610.1134/S1070363224020075
     [Google Scholar]
  68. RavindraS. JesinC.P.I. HariprasadR. NatarajanK. PriyaV.R.P. NandiG.C. Sulfonimidamide as directing group for Pd‐mediated ortho‐C−H chlorination of arenes.ChemistrySelect202493e20230425310.1002/slct.202304253
     [Google Scholar]
  69. KonaC.N. OkuR. NakamuraS. MiuraM. HiranoK. NishiiY. Aromatic halogenation using carborane catalyst.Chem202410140241310.1016/j.chempr.2023.10.006
     [Google Scholar]
  70. TanemuraK. Halogenation of aromatic compounds with N -halosuccinimides (NXS) catalysed by d -camphorsulfonic acid-BiCl 3.Org. Biomol. Chem.202422255105511110.1039/D4OB00837E38864412
     [Google Scholar]
  71. HanH. QinY. WangF. DingN. FangF. HuL. JinH. ZhangY. Two-step synthesis of 4-hydroxy-3,5-dimethylphenyl benzoate: Undergraduate organic laboratory of electrophilic aromatic substitution and nucleophilic aromatic substitution.J. Chem. Educ.202410162406241210.1021/acs.jchemed.3c01270
     [Google Scholar]
  72. ChenC. AndreaniT. LiH. A divergent and selective synthesis of isomeric benzoxazoles from a single N-Cl imine.Org. Lett.201113236300630310.1021/ol202844c22067007
     [Google Scholar]
  73. CadoniR. PorchedduA. GiacomelliG. De LucaL. One-pot synthesis of amides from aldehydes and amines via C-H bond activation.Org. Lett.201214195014501710.1021/ol302175v22978698
     [Google Scholar]
  74. ChengJ.H. RameshC. KaoH.L. WangY.J. ChanC.C. LeeC.F. Synthesis of aryl thioethers through the N-chlorosuccinimide-promoted cross-coupling reaction of thiols with Grignard reagents.J. Org. Chem.20127722103691037410.1021/jo302088t23067042
     [Google Scholar]
  75. XuJ. YangZ. Convenient and environment-friendly synthesis of sulfonyl chlorides from S-alkylisothiourea salts via N-chlorosuccinimide chlorosulfonation.Synthesis201345121675168210.1055/s‑0033‑1338743
     [Google Scholar]
  76. NishiguchiA. MaedaK. MikiS. Sulfonyl chloride formation from thiol derivatives by N-chlorosuccinimide mediated oxidation.Synthesis20062006244131413410.1055/s‑2006‑950353
     [Google Scholar]
  77. VeisiH. Ghorbani-VagheiR. HemmatiS. MahmoodiJ. Convenient one-pot synthesis of sulfonamides and sulfonyl azides from thiols using N-chlorosuccinimide.Synlett20112011162315232010.1055/s‑0030‑1261232
     [Google Scholar]
  78. Silva-CuevasC. Perez-ArrietaC. Polindara-GarcíaL.A. Lujan-MontelongoJ.A. Sulfonyl halide synthesis by thiol oxyhalogenation using NBS/NCS – i PrOH.Tetrahedron Lett.201758232244224710.1016/j.tetlet.2017.04.087
     [Google Scholar]
  79. García-DomínguezA. WestN.M. HembreR.T. Lloyd-JonesG.C. Thiol chlorination with N -chlorosuccinimide: HCl-catalyzed release of molecular chlorine and the dichotomous effects of water.ACS Catal.202313149487949410.1021/acscatal.3c02380
     [Google Scholar]
  80. GaspaS. PorchedduA. ValentoniA. GarroniS. EnzoS. De LucaL. A mechanochemical‐assisted oxidation of amines to carbonyl compounds and nitriles.Eur. J. Org. Chem.20172017375519552610.1002/ejoc.201700689
     [Google Scholar]
  81. TerhorstS. JansenT. LangletzT. BolmC. Sulfonimidamides by sequential mechanochemical chlorinations and aminations of sulfinamides.Org. Lett.202224234109411310.1021/acs.orglett.2c0109935658444
     [Google Scholar]
  82. YangZ. HeJ. WeiY. LiW. LiuP. ZhaoJ. WeiY. NCS-promoted thiocyanation and selenocyanation of pyrrolo[1,2-a]quinoxalines.Org. Biomol. Chem.202018449088909410.1039/D0OB01818J33146224
     [Google Scholar]
  83. PrajapatiR.V. PrajapatiV.D. PurohitV.B. Andre BaptistaL. AvalaniJ.R. SapariyaN.H. KaradS.C. RavalD.K. N ‐chlorosuccinimide mediated direct C−H thiocyanation of 1‐aryl‐5‐pyrazolones at room temperature.ChemistrySelect2023822e20230101810.1002/slct.202301018
     [Google Scholar]
  84. SahaS. PinheiroA.B. ChatterjeeA. BhutiaZ.T. BanerjeeM. A solvent-free mechanochemical electrophilic C–H thiocyanation of indoles and imidazo[1,2-a]pyridines using a cost-effective combination of N -chlorosuccinimide-NaSCN and tandem C–C and C–S bond formation.Green Chem.202426105879588910.1039/D4GC00486H
     [Google Scholar]
  85. KaewsriW. ThongsornkleebC. TummatornJ. RuchirawatS. Isomerizable (E/Z)-alkynyl-O-methyl oximes employing TMSCl–NCS in chlorinative cyclization for the direct synthesis of 4-chloroisoxazoles.RSC Advances2016654486664867510.1039/C6RA09396E
     [Google Scholar]
  86. WangA.F. ZhuY.L. WangS.L. HaoW.J. LiG. TuS.J. JiangB. Metal-free radical haloazidation of benzene-tethered 1, 7-enynes leading to polyfunctionalized 3, 4-dihydroquinolin-2 (1 H)-ones.J. Org. Chem.20168131099110510.1021/acs.joc.5b0265526716579
     [Google Scholar]
  87. NorseedaK. ChaisanN. ThongsornkleebC. TummatornJ. RuchirawatS. Metal-free synthesis of 4-chloroisocoumarins by TMSCl-catalyzed NCS-induced chlorinative annulation of 2-alkynylaryloate esters.J. Org. Chem.20198424162221623610.1021/acs.joc.9b0279331742402
     [Google Scholar]
  88. PramanikM. MathuriA. SauS. DasM. MalP. Chlorinative cyclization of aryl alkynoates using NCS and 9-mesityl-10-methylacridinium perchlorate photocatalyst.Org. Lett.202123208088809210.1021/acs.orglett.1c0310034558906
     [Google Scholar]
  89. ZhangY. HeY. LiuT. GuoW. Modular divergent synthesis of functionalized indoles via TFA-promoted amino-claisen rearrangement at room temperature.Org. Lett.202325152680268410.1021/acs.orglett.3c0076437021829
     [Google Scholar]
  90. JiaY. AblajanK. N‐chlorosuccinimide‐promoted one‐pot synthesis of substituted 4,5‐dihydroisoxazole‐5‐methanols in aqueous medium.Adv. Synth. Catal.2023365224425110.1002/adsc.202200999
     [Google Scholar]
  91. MasuyamaY. KobayashiY. YanagiR. KurusuY. Aldol-type reaction by propen-2-yl acetate with NCS/SnCl2/ROH.Chem. Lett.199221102039204210.1246/cl.1992.2039
     [Google Scholar]
  92. BandgarB.P. KundeM.L.B. ThoteJ.L. Deoximation with N-Haloamides.Synth. Commun.19972771149115210.1080/00397919708003350
     [Google Scholar]
  93. IranpoorN. FirouzabadiH. AghapourG. A rapid and facile conversion of primary amides and aldoximes to nitriles and ketoximes to amides with triphenylphosphine and N-chlorosuccinimide.Synth. Commun.200232162535254110.1081/SCC‑120005936
     [Google Scholar]
  94. GucmaM. GołebiewskiW.M. Convenient conversion of aldoximes into nitriles with N-chlorosuccinimide and pyridine.Synthesis20081319971999
     [Google Scholar]
  95. YadavJ.S. Subba ReddyB.V. JainR. BaishyaG. N-Chlorosuccinimide as a versatile reagent for the sulfenylation of ketones: A facile synthesis of α-ketothioethers.Tetrahedron Lett.200849183015301810.1016/j.tetlet.2008.02.136
     [Google Scholar]
  96. Antoine JohnA. LinQ. Synthesis of azobenzenes using N-chlorosuccinimide and 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU).J. Org. Chem.201782189873987610.1021/acs.joc.7b0153028846399
     [Google Scholar]
  97. MohiteA.R. PhatakeR.S. DubeyP. AgbariaM. ShamesA.I. LemcoffN.G. ReanyO. Thiourea-mediated halogenation of alcohols.J. Org. Chem.20208520129011291110.1021/acs.joc.0c0143132938176
     [Google Scholar]
  98. GovaertsS. AngeliniL. HamptonC. Malet-SanzL. RuffoniA. LeonoriD. Photoinduced olefin diamination with alkylamines.Angew. Chem. Int. Ed.20205935150211502810.1002/anie.20200565232432808
     [Google Scholar]
  99. ZhangS. ZhangQ. TangM. Synthesis of hydrazides from N-tosylhydrazones and its application in the preparation of indazolones.J. Org. Chem.20228753845385010.1021/acs.joc.1c0303735084186
     [Google Scholar]
  100. ZhangF. LuoY. LiuY. YangW. XuJ. Straightforward access to C2-formyl indoles using an oxidative combination of N-chlorosuccinimide and dimethyl sulfoxide.Tetrahedron202415913400510.1016/j.tet.2024.134005
     [Google Scholar]
  101. PatiS.S. MishraA. DasJ.P. Regio-and stereocontrolled hydrohalogenation of ynamides with N-halosuccinimides (NXS) as the halogen source: Synthesis of (E)-α-haloenamides.J. Org. Chem.2024893acs.joc.3c0243610.1021/acs.joc.3c0243638237061
     [Google Scholar]
/content/journals/coc/10.2174/0113852728332929240920061326
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N-Chlorosuccinimide: A Versatile Reagent in Organic Synthesis
Current Organic Chemistry 29, 936 (2025); https://doi.org/10.2174/0113852728332929240920061326
/content/journals/coc/10.2174/0113852728332929240920061326
/content/journals/coc/10.2174/0113852728332929240920061326
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  • Article Type:     Review Article
Keyword(s): chlorination; haloalkanes; haloarenes; N-chlorosuccinimide; N-halosuccinimide; oxidation

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