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image of N-Chlorosuccinimide: A Versatile Reagent in Organic Synthesis

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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2024-10-29
2025-01-18
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References

  1. Chauhan P. N-Chlorosuccinimide (NCS). Synlett 2010 2010 8 1285 1286 10.1055/s‑0029‑1219581
    [Google Scholar]
  2. Tscherniac J. Knowledge of chlorimides. Ber. Dtsch. Chem. Ges. 1901 34 3 4209 4214 10.1002/cber.190103403152
    [Google Scholar]
  3. Zimmer H. Audrieth L.F. Tertiary butyl hypochlorite as as N-chlorinating agent. J. Am. Chem. Soc. 1954 76 14 3856 3857 10.1021/ja01643a082
    [Google Scholar]
  4. Virgil S.C. N-Chlorosuccinimide. Encyclopedia of Reagents for Organic Synthesis John Wiley & Sons New York. 1995 1 768 773
    [Google Scholar]
  5. Bretheric L. Handbook of Reactive Chemical Hazards. 5th ed London Butterworth-Heinemann 1995
    [Google Scholar]
  6. Fieser M. Fieser L.F. Reagents for organic synthesis. John Wiley & Sons 1974
    [Google Scholar]
  7. Gołebiewski W. Gucma M. Applications of N-chlorosuccinimide in organic synthesis. Synthesis 2007 2007 23 3599 3619 10.1055/s‑2007‑990871
    [Google Scholar]
  8. Kim K.S. Cho I.H. Yoo B.K. Song Y.H. Hahn C.S. Selective oxidation of primary and secondary alcohols using di-isopropyl sulphide–N-chlorosuccinimide. J. Chem. Soc. Chem. Commun. 1984 12 12 762 763 10.1039/C39840000762
    [Google Scholar]
  9. Kohl H.H. Wheatley W.B. Worley S.D. Bodor N. Antimicrobial activity of N-chloramine compounds. J. Pharm. Sci. 1980 69 11 1292 1295 10.1002/jps.2600691116 7005422
    [Google Scholar]
  10. Juenge E.C. Spangler P.L. Duncan W.P. The reaction of 1,3,5-Trichloro-2,4,6-trioxo-hexahydro-s-triazine with tetrahydrofuran and related cyclic ethers. J. Org. Chem. 1966 31 11 3836 3838 10.1021/jo01349a503
    [Google Scholar]
  11. Singh Z. Kaur J. Kaur R. Hundal S.S. Toxic effects of organochlorine pesticides: A review. Am. J. Biomed. Sci. 2016 4 11
    [Google Scholar]
  12. Lee J.C. Bae Y.H. Chang S.K. Efficient alpha-halogenation of carbonyl compounds by N-bromosuccinimide and N-chlorosuccinimde. Bull. Korean Chem. Soc. 2003 24 4 407 408 10.5012/bkcs.2003.24.4.407
    [Google Scholar]
  13. Meshram H.M. Reddy P.N. Sadashiv K. Yadav J.S. Amberlyst-15®-promoted efficient 2-halogenation of 1,3-keto-esters and cyclic ketones using N-halosuccinimides. Tetrahedron Lett. 2005 46 4 623 626 10.1016/j.tetlet.2004.11.140
    [Google Scholar]
  14. Mellegaard-Waetzig S.R. Wang C. Tunge J.A. Selenium-catalyzed oxidative halogenation. Tetrahedron 2006 62 30 7191 7198 10.1016/j.tet.2005.12.072
    [Google Scholar]
  15. Ley S.V. Whittle A.J. A convenient preparation of 2-haloenones from enones using phenylselenium halides. Tetrahedron Lett. 1981 22 34 3301 3304 10.1016/S0040‑4039(01)81890‑6
    [Google Scholar]
  16. Murphy M. Lynch D. Schaeffer M. Kissane M. Chopra J. O’Brien E. Ford A. Ferguson G. Maguire A.R. Investigation of the synthetic and mechanistic aspects of the highly stereoselective transformation of α-thioamides to α-thio-β-chloroacrylamides. Org. Biomol. Chem. 2007 5 8 1228 1241 10.1039/B618540A 17406721
    [Google Scholar]
  17. Mei Y. Bentley P.A. Du J. Thiourea catalysis of NCS in the synthesis of α-chloroketones. Tetrahedron Lett. 2008 49 23 3802 3804 10.1016/j.tetlet.2008.03.154
    [Google Scholar]
  18. Wittkopp A. Schreiner P.R. Metal-free, noncovalent catalysis of diels-alder reactions by neutral hydrogen bond donors in organic solvents and in water. Chemistry 2003 9 2 407 414 10.1002/chem.200390042 12532289
    [Google Scholar]
  19. Schreiner P.R. Wittkopp A. H-bonding additives act like Lewis acid catalysts. Org. Lett. 2002 4 2 217 220 10.1021/ol017117s 11796054
    [Google Scholar]
  20. Okino T. Hoashi Y. Takemoto Y. Thiourea-catalyzed nucleophilic addition of TMSCN and ketene silyl acetals to nitrones and aldehydes. Tetrahedron Lett. 2003 44 14 2817 2821 10.1016/S0040‑4039(03)00433‑7
    [Google Scholar]
  21. Sohtome Y. Tanatani A. Hashimoto Y. Nagasawa K. Development of novel chiral urea catalysts for the hetero-Michael reaction. Chem. Pharm. Bull. 2004 52 4 477 480 10.1248/cpb.52.477 15056971
    [Google Scholar]
  22. Maher D.J. Connon S.J. Acceleration of the DABCO-promoted Baylis–Hillman reaction using a recoverable H-bonding organocatalyst. Tetrahedron Lett. 2004 45 6 1301 1305 10.1016/j.tetlet.2003.11.062
    [Google Scholar]
  23. Menche D. Hassfeld J. Li J. Menche G. Ritter A. Rudolph S. Hydrogen bond catalyzed direct reductive amination of ketones. Org. Lett. 2006 8 4 741 744 10.1021/ol053001a 16468756
    [Google Scholar]
  24. Hoashi Y. Okino T. Takemoto Y. Enantioselective Michael addition to α,β-unsaturated imides catalyzed by a bifunctional organocatalyst. Angew. Chem. Int. Ed. 2005 44 26 4032 4035 10.1002/anie.200500459 15906403
    [Google Scholar]
  25. Veeneman G.H. van Leeuwen S.H. van Boom J.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. 1990 31 9 1331 1334 10.1016/S0040‑4039(00)88799‑7
    [Google Scholar]
  26. Bentley P.A. Mei Y. Du J. Thiourea catalysis of NCS in the synthesis of β-chloroethers. Tetrahedron Lett. 2008 49 16 2653 2655 10.1016/j.tetlet.2008.02.040
    [Google Scholar]
  27. Pravst I. Zupan M. Stavber S. Halogenation of ketones with N-halosuccinimides under solvent-free reaction conditions. Tetrahedron 2008 64 22 5191 5199 10.1016/j.tet.2008.03.048
    [Google Scholar]
  28. Zheng Z. Han B. Wu F. Shi T. Liu J. Zhang Y. Hao J. One-step for the preparation of α-haloacetal of ketones with N-bromosuccinimide/N-chlorosuccinimide (NBS/NCS) and ethylene glycol. Tetrahedron 2016 72 48 7738 7743 10.1016/j.tet.2016.05.064
    [Google Scholar]
  29. Ke Z. Lam Y.P. Chan K.S. Yeung Y.Y. Zwitterion-catalyzed deacylative dihalogenation of β-oxo amides. Org. Lett. 2020 22 18 7353 7357 10.1021/acs.orglett.0c02701 32870014
    [Google Scholar]
  30. Lebarillier L. Outurquin F. Paulmier C. Synthesis and reactivity of α- and β-Chloro-α-phenylselanyl Esters. Tetrahedron 2000 56 38 7495 7502 10.1016/S0040‑4020(00)00648‑7
    [Google Scholar]
  31. Bernardi L. Jørgensen K.A. Enantioselective chlorination and fluorination of β-keto phosphonates catalyzed by chiral Lewis acids. Chem. Commun. 2005 10 10 1324 1326 10.1039/B415568H 15742066
    [Google Scholar]
  32. Zhao M.X. Zhang Z.W. Chen M.X. Tang W.H. Shi M. Cinchona alkaloid catalyzed enantioselective chlorination of 3‐aryloxindoles. Eur. J. Org. Chem. 2011 2011 16 3001 3008 10.1002/ejoc.201100061
    [Google Scholar]
  33. Liu K.C. Shelton B.R. Howe R.K. A particularly convenient preparation of benzohydroximinoyl chlorides (nitrile oxide precursors). J. Org. Chem. 1980 45 19 3916 3918 10.1021/jo01307a039
    [Google Scholar]
  34. Foley D.A. Doecke C.W. Buser J.Y. Merritt J.M. Murphy L. Kissane M. Collins S.G. Maguire A.R. Kaerner A. 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. 2011 76 23 9630 9640 10.1021/jo201212p 22029382
    [Google Scholar]
  35. Schwarz L. Girreser U. Clement B. Synthesis and characterization of para‐Substituted N, N′‐Dihydroxybenzamidines and their derivatives as model compounds for a class of prodrugs. Eur. J. Org. Chem. 2014 2014 9 1961 1975 10.1002/ejoc.201301622
    [Google Scholar]
  36. Wingard L.A. Guzmán P.E. Sabatini J.J. A chlorine gas-free synthesis of dichloroglyoxime. Org. Process Res. Dev. 2016 20 9 1686 1688 10.1021/acs.oprd.6b00252
    [Google Scholar]
  37. Hernández-Calva A. Meléndez-Balbuena L. Arroyo-Carranza M. Ramírez-Monroy A. Halogenation of aldoximes. A versatile reaction for the synthesis of highly functionalized hydroximoyl chlorides and furazan N-oxides. Russ. J. Org. Chem. 2023 59 12 2221 2229 10.1134/S1070428023120217
    [Google Scholar]
  38. Yamane T. Mitsudera H. Shundoh T. 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. Synthesis 2004 2004 17 2825 2832 10.1055/s‑2004‑834862
    [Google Scholar]
  39. Yamane T. Mitsudera H. Shundoh T. Highly regioselective direct halogenation: A simple and efficient method for preparing 4-halomethyl-5-methyl-2-aryl-1,3-thiazoles. Tetrahedron Lett. 2004 45 1 69 73 10.1016/j.tetlet.2003.10.113
    [Google Scholar]
  40. Jacobs J. Van T.N. Stevens C.V. Markusse P. De Cooman P. Maat L. De Kimpe N. 1,4-Dehydrochlorination of 1-(1-haloalkyl)-3,4-dihydroisoquinolines as a convenient route to functionalized isoquinolines. Tetrahedron Lett. 2009 50 26 3698 3701 10.1016/j.tetlet.2009.03.211
    [Google Scholar]
  41. Liu X. Wang Y. Chen S. Jia Q. Wang G. Li S. Direct benzylic polychlorination of (poly)azines with N -chlorosuccinimide. Org. Chem. Front. 2023 10 13 3336 3340 10.1039/D3QO00611E
    [Google Scholar]
  42. Yoshimitsu T. Fukumoto N. Tanaka T. Enantiocontrolled synthesis of polychlorinated hydrocarbon motifs: A nucleophilic multiple chlorination process revisited. J. Org. Chem. 2009 74 2 696 702 10.1021/jo802093d 19053592
    [Google Scholar]
  43. Pimenta L.S. Gusevskaya E.V. Alberto E.E. Intermolecular halogenation/esterification of alkenes with N ‐halosuccinimide and acetic acid catalyzed by 1,4‐diazabicyclo[2.2.2]octane. Adv. Synth. Catal. 2017 359 13 2297 2303 10.1002/adsc.201700117
    [Google Scholar]
  44. Bentley P.A. Mei Y. Du J. Thiourea catalysis of NCS in the synthesis of chlorohydrins. Tetrahedron Lett. 2008 49 8 1425 1427 10.1016/j.tetlet.2007.11.211
    [Google Scholar]
  45. Murray R.E. A high yield procedure for 1-chloro-1-alkynes. Synth. Commun. 1980 10 5 345 349 10.1080/00397918008061822
    [Google Scholar]
  46. Bucos M. Villalonga-Barber C. Micha-Screttas M. Steele B.R. Screttas C.G. Heropoulos G.A. Microwave assisted solid additive effects in simple dry chlorination reactions with n-chlorosuccinimide. Tetrahedron 2010 66 11 2061 2065 10.1016/j.tet.2010.01.033
    [Google Scholar]
  47. Li Z.H. Fiser B. Jiang B.L. Li J.W. Xu B.H. Zhang S.J. N -Hydroxyphthalimide/benzoquinone-catalyzed chlorination of hydrocarbon C–H bond using N -chlorosuccinimide. Org. Biomol. Chem. 2019 17 13 3403 3408 10.1039/C9OB00216B 30869109
    [Google Scholar]
  48. Xiang M. Zhou C. Yang X.L. Chen B. Tung C.H. Wu L.Z. Visible light-catalyzed benzylic C–H bond chlorination by a combination of organic dye (Acr+-Mes) and N-chlorosuccinimide. J. Org. Chem. 2020 85 14 9080 9087 10.1021/acs.joc.0c01000 32434320
    [Google Scholar]
  49. Weinzierl D. Piringer M. Zebrowski P. Stockhammer L. Waser M. Photochemical wolff rearrangement initiated generation and subsequent α-chlorination of C1 ammonium enolates. Org. Lett. 2023 25 17 3126 3130 10.1021/acs.orglett.3c00986 37098273
    [Google Scholar]
  50. Liao S. Liang J. Li C. Chen N. Yang K. Chen J. Song Q. Synthesis of α-haloboronates by the halogenation of gem-diborylalkanes via tetracoordinate boron species. Org. Lett. 2023 25 16 2928 2933 10.1021/acs.orglett.3c00982 37071548
    [Google Scholar]
  51. Xing R.G. Li Y.N. Zhang B.W. Preparation of chloro-functionalized reduced graphene oxide by silver-catalyzed radical reaction. Chin. Chem. Lett. 2017 28 2 407 411 10.1016/j.cclet.2016.10.017
    [Google Scholar]
  52. Zhang Y. Shibatomi K. Yamamoto H. Lewis acid catalyzed highly selective halogenation of aromatic compounds. Synlett 2005 18 2837 2842
    [Google Scholar]
  53. Du B. Jiang X. Sun P. 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. 2013 78 6 2786 2791 10.1021/jo302765g 23373558
    [Google Scholar]
  54. Kalyani D. Dick A.R. Anani W.Q. Sanford M.S. A simple catalytic method for the regioselective halogenation of arenes. Org. Lett. 2006 8 12 2523 2526 10.1021/ol060747f 16737304
    [Google Scholar]
  55. Li J.T. Wang L.X. Wang D.X. Zhao L. Wang M.X. Synthesis, resolution, structure, and racemization of inherently chiral 1,3-alternate azacalix[4]pyrimidines: Quantification of conformation mobility. J. Org. Chem. 2014 79 5 2178 2188 10.1021/jo500054v 24512534
    [Google Scholar]
  56. Li B. Liu B. Shi B.F. Copper-catalyzed ortho-halogenation of arenes and heteroarenes directed by a removable auxiliary. Chem. Commun. 2015 51 24 5093 5096 10.1039/C5CC00531K 25712552
    [Google Scholar]
  57. Samanta R.C. Yamamoto H. Selective halogenation using an aniline catalyst. Chemistry 2015 21 34 11976 11979 10.1002/chem.201502234 26185028
    [Google Scholar]
  58. Maddox S.M. Nalbandian C.J. Smith D.E. Gustafson J.L. A practical Lewis base catalyzed electrophilic chlorination of arenes and heterocycles. Org. Lett. 2015 17 4 1042 1045 10.1021/acs.orglett.5b00186 25671756
    [Google Scholar]
  59. Bovonsombat P. Sophanpanichkul P. Pandey A. Tungsirisurp S. Limthavornlit P. Chobtumskul K. Kuhataparuk P. Sathityatiwat S. Teecomegaet P. Novel regioselective aromatic chlorination via catalytic thiourea activation of N-chlorosuccinimide. Tetrahedron Lett. 2015 56 17 2193 2196 10.1016/j.tetlet.2015.03.034
    [Google Scholar]
  60. Moghaddam F.M. Tavakoli G. Saeednia B. Langer P. Jafari B. Palladium-catalyzed carbamate-directed regioselective halogenation: A route to halogenated anilines. J. Org. Chem. 2016 81 9 3868 3876 10.1021/acs.joc.6b00329 27072283
    [Google Scholar]
  61. Hering T. König B. Photocatalytic activation of N-chloro compounds for the chlorination of arenes. Tetrahedron 2016 72 48 7821 7825 10.1016/j.tet.2016.06.028
    [Google Scholar]
  62. Tang R.J. Milcent T. Crousse B. Regioselective halogenation of arenes and heterocycles in hexafluoroisopropanol. J. Org. Chem. 2018 83 2 930 938 10.1021/acs.joc.7b02920 29256248
    [Google Scholar]
  63. Rogers D.A. Gallegos J.M. Hopkins M.D. Lignieres A.A. Pitzel A.K. Lamar A.A. Visible-light photocatalytic activation of N-chlorosuccinimide by organic dyes for the chlorination of arenes and heteroarenes. Tetrahedron 2019 75 36 130498 10.1016/j.tet.2019.130498
    [Google Scholar]
  64. Ivanova Y.B. Chizhova N.V. Shumilova I.A. Rusanov A.I. Mamardashvili N.Z. Acid–base properties of polyhalogenated tetraphenylporphyrins. Russ. J. Org. Chem. 2020 56 6 1054 1061 10.1134/S1070428020060147
    [Google Scholar]
  65. Matsuoka J. Yano Y. Hirose Y. Mashiba K. Sawada N. Nakamura A. Maegawa T. Elemental sulfur-mediated aromatic halogenation. J. Org. Chem. 2024 89 1 770 777 10.1021/acs.joc.3c02259 38113515
    [Google Scholar]
  66. Xu J. Li X. Li Q. Tian W. Yang X. Dabco-catalysed selective chlorination of aromatics. Tetrahedron Lett. 2024 136 154928 10.1016/j.tetlet.2024.154928
    [Google Scholar]
  67. Stroganova T.A. Vasilin V.K. Shitikov N.V. Dmitrieva I.G. Krapivin G.D. 3-Aminofuro[2,3-b]pyridines: Reaction with N-chlorosuccinimide and sodium hypochlorite. Russ. J. Gen. Chem. 2024 94 2 314 326 10.1134/S1070363224020075
    [Google Scholar]
  68. Ravindra S. Jesin C.P.I. Hariprasad R. Natarajan K. Priya V.R.P. Nandi G.C. Sulfonimidamide as directing group for Pd‐mediated ortho‐C−H chlorination of arenes. ChemistrySelect 2024 9 3 e202304253 10.1002/slct.202304253
    [Google Scholar]
  69. Kona C.N. Oku R. Nakamura S. Miura M. Hirano K. Nishii Y. Aromatic halogenation using carborane catalyst. Chem 2024 10 1 402 413 10.1016/j.chempr.2023.10.006
    [Google Scholar]
  70. Tanemura K. Halogenation of aromatic compounds with N -halosuccinimides (NXS) catalysed by d -camphorsulfonic acid-BiCl 3. Org. Biomol. Chem. 2024 22 25 5105 5111 10.1039/D4OB00837E 38864412
    [Google Scholar]
  71. Han H. Qin Y. Wang F. Ding N. Fang F. Hu L. Jin H. Zhang Y. Two-step synthesis of 4-hydroxy-3,5-dimethylphenyl benzoate: undergraduate organic laboratory of electrophilic aromatic substitution and nucleophilic aromatic substitution. J. Chem. Educ. 2024 101 6 2406 2412 10.1021/acs.jchemed.3c01270
    [Google Scholar]
  72. Chen C. Andreani T. Li H. A divergent and selective synthesis of isomeric benzoxazoles from a single N-Cl imine. Org. Lett. 2011 13 23 6300 6303 10.1021/ol202844c 22067007
    [Google Scholar]
  73. Cadoni R. Porcheddu A. Giacomelli G. De Luca L. One-pot synthesis of amides from aldehydes and amines via C-H bond activation. Org. Lett. 2012 14 19 5014 5017 10.1021/ol302175v 22978698
    [Google Scholar]
  74. Cheng J.H. Ramesh C. Kao H.L. Wang Y.J. Chan C.C. Lee C.F. Synthesis of aryl thioethers through the N-chlorosuccinimide-promoted cross-coupling reaction of thiols with Grignard reagents. J. Org. Chem. 2012 77 22 10369 10374 10.1021/jo302088t 23067042
    [Google Scholar]
  75. Xu J. Yang Z. Convenient and environment-friendly synthesis of sulfonyl chlorides from S-alkylisothiourea salts via N-chlorosuccinimide chlorosulfonation. Synthesis 2013 45 12 1675 1682 10.1055/s‑0033‑1338743
    [Google Scholar]
  76. Nishiguchi A. Maeda K. Miki S. Sulfonyl chloride formation from thiol derivatives by N-chlorosuccinimide mediated oxidation. Synthesis 2006 2006 24 4131 4134 10.1055/s‑2006‑950353
    [Google Scholar]
  77. Veisi H. Ghorbani-Vaghei R. Hemmati S. Mahmoodi J. Convenient one-pot synthesis of sulfonamides and sulfonyl azides from thiols using N-chlorosuccinimide. Synlett 2011 2011 16 2315 2320 10.1055/s‑0030‑1261232
    [Google Scholar]
  78. Silva-Cuevas C. Perez-Arrieta C. Polindara-García L.A. Lujan-Montelongo J.A. Sulfonyl halide synthesis by thiol oxyhalogenation using NBS/NCS – i PrOH. Tetrahedron Lett. 2017 58 23 2244 2247 10.1016/j.tetlet.2017.04.087
    [Google Scholar]
  79. García-Domínguez A. West N.M. Hembre R.T. Lloyd-Jones G.C. Thiol chlorination with N -chlorosuccinimide: HCl-catalyzed release of molecular chlorine and the dichotomous effects of water. ACS Catal. 2023 13 14 9487 9494 10.1021/acscatal.3c02380
    [Google Scholar]
  80. Gaspa S. Porcheddu A. Valentoni A. Garroni S. Enzo S. De Luca L. A mechanochemical‐assisted oxidation of amines to carbonyl compounds and nitriles. Eur. J. Org. Chem. 2017 2017 37 5519 5526 10.1002/ejoc.201700689
    [Google Scholar]
  81. Terhorst S. Jansen T. Langletz T. Bolm C. Sulfonimidamides by sequential mechanochemical chlorinations and aminations of sulfinamides. Org. Lett. 2022 24 23 4109 4113 10.1021/acs.orglett.2c01099 35658444
    [Google Scholar]
  82. Yang Z. He J. Wei Y. Li W. Liu P. Zhao J. Wei Y. NCS-promoted thiocyanation and selenocyanation of pyrrolo[1,2- a ]quinoxalines. Org. Biomol. Chem. 2020 18 44 9088 9094 10.1039/D0OB01818J 33146224
    [Google Scholar]
  83. Prajapati R.V. Prajapati V.D. Purohit V.B. Andre Baptista L. Avalani J.R. Sapariya N.H. Karad S.C. Raval D.K. N ‐chlorosuccinimide mediated direct c−h thiocyanation of 1‐aryl‐5‐pyrazolones at room temperature. ChemistrySelect 2023 8 22 e202301018 10.1002/slct.202301018
    [Google Scholar]
  84. Saha S. Pinheiro A.B. Chatterjee A. Bhutia Z.T. Banerjee M. 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. 2024 26 10 5879 5889 10.1039/D4GC00486H
    [Google Scholar]
  85. Kaewsri W. Thongsornkleeb C. Tummatorn J. Ruchirawat S. Isomerizable (E/Z)-alkynyl-O-methyl oximes employing TMSCl–NCS in chlorinative cyclization for the direct synthesis of 4-chloroisoxazoles. RSC Advances 2016 6 54 48666 48675 10.1039/C6RA09396E
    [Google Scholar]
  86. Wang A.F. Zhu Y.L. Wang S.L. Hao W.J. Li G. Tu S.J. Jiang B. Metal-free radical haloazidation of benzene-tethered 1, 7-enynes leading to polyfunctionalized 3, 4-dihydroquinolin-2 (1 H)-ones. J. Org. Chem. 2016 81 3 1099 1105 10.1021/acs.joc.5b02655 26716579
    [Google Scholar]
  87. Norseeda K. Chaisan N. Thongsornkleeb C. Tummatorn J. Ruchirawat S. Metal-free synthesis of 4-chloroisocoumarins by TMSCl-catalyzed NCS-induced chlorinative annulation of 2-alkynylaryloate esters. J. Org. Chem. 2019 84 24 16222 16236 10.1021/acs.joc.9b02793 31742402
    [Google Scholar]
  88. Pramanik M. Mathuri A. Sau S. Das M. Mal P. Chlorinative cyclization of aryl alkynoates using NCS and 9-mesityl-10-methylacridinium perchlorate photocatalyst. Org. Lett. 2021 23 20 8088 8092 10.1021/acs.orglett.1c03100 34558906
    [Google Scholar]
  89. Zhang Y. He Y. Liu T. Guo W. Modular divergent synthesis of functionalized indoles via TFA-promoted amino-claisen rearrangement at room temperature. Org. Lett. 2023 25 15 2680 2684 10.1021/acs.orglett.3c00764 37021829
    [Google Scholar]
  90. Jia Y. Ablajan K. N‐chlorosuccinimide‐promoted one‐pot synthesis of substituted 4,5‐dihydroisoxazole‐5‐methanols in aqueous medium. Adv. Synth. Catal. 2023 365 2 244 251 10.1002/adsc.202200999
    [Google Scholar]
  91. Masuyama Y. Kobayashi Y. Yanagi R. Kurusu Y. Aldol-type reaction by propen-2-yl acetate with NCS/SnCl2/ROH. Chem. Lett. 1992 21 10 2039 2042 10.1246/cl.1992.2039
    [Google Scholar]
  92. Bandgar B.P. Kunde M.L.B. Thote J.L. Deoximation with N-Haloamides. Synth. Commun. 1997 27 7 1149 1152 10.1080/00397919708003350
    [Google Scholar]
  93. Iranpoor N. Firouzabadi H. Aghapour G. A rapid and facile conversion of primary amides and aldoximes to nitriles and ketoximes to amides with triphenylphosphine and N-chlorosuccinimide. Synth. Commun. 2002 32 16 2535 2541 10.1081/SCC‑120005936
    [Google Scholar]
  94. Gucma M. Gołebiewski W.M. Convenient conversion of aldoximes into nitriles with N-chlorosuccinimide and pyridine. Synthesis 2008 13 1997 1999
    [Google Scholar]
  95. Yadav J.S. Subba Reddy B.V. Jain R. Baishya G. N-Chlorosuccinimide as a versatile reagent for the sulfenylation of ketones: A facile synthesis of α-ketothioethers. Tetrahedron Lett. 2008 49 18 3015 3018 10.1016/j.tetlet.2008.02.136
    [Google Scholar]
  96. Antoine John A. Lin Q. Synthesis of azobenzenes using N-chlorosuccinimide and 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU). J. Org. Chem. 2017 82 18 9873 9876 10.1021/acs.joc.7b01530 28846399
    [Google Scholar]
  97. Mohite A.R. Phatake R.S. Dubey P. Agbaria M. Shames A.I. Lemcoff N.G. Reany O. Thiourea-mediated halogenation of alcohols. J. Org. Chem. 2020 85 20 12901 12911 10.1021/acs.joc.0c01431 32938176
    [Google Scholar]
  98. Govaerts S. Angelini L. Hampton C. Malet-Sanz L. Ruffoni A. Leonori D. Photoinduced olefin diamination with alkylamines. Angew. Chem. Int. Ed. 2020 59 35 15021 15028 10.1002/anie.202005652 32432808
    [Google Scholar]
  99. Zhang S. Zhang Q. Tang M. Synthesis of hydrazides from N-tosylhydrazones and its application in the preparation of indazolones. J. Org. Chem. 2022 87 5 3845 3850 10.1021/acs.joc.1c03037 35084186
    [Google Scholar]
  100. Zhang F. Luo Y. Liu Y. Yang W. Xu J. Straightforward access to C2-formyl indoles using an oxidative combination of N-chlorosuccinimide and dimethyl sulfoxide. Tetrahedron 2024 159 134005 10.1016/j.tet.2024.134005
    [Google Scholar]
  101. Pati S.S. Mishra A. Das J.P. Regio-and stereocontrolled hydrohalogenation of ynamides with N-halosuccinimides (NXS) as the halogen source: Synthesis of (E)-α-haloenamides. J. Org. Chem. 2024 89 3 acs.joc.3c02436 10.1021/acs.joc.3c02436 38237061
    [Google Scholar]
/content/journals/coc/10.2174/0113852728332929240920061326
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  • Article Type:
    Review Article
Keywords: N-chlorosuccinimide ; chlorination ; haloarenes ; haloalkanes ; oxidation ; N-halosuccinimide
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