Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Efficient α-Halogenation of Carbonyl Compounds by N-Bromosuccinimide and N-Chlorosuccinimde

  • Published : 2003.04.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. De Kimpe, N.; Verhé, R. In The Chemistry of a-Haloketones, ${\alpha}$-Haloaldehydes and ${\alpha}$-Haloimines; Patai, S.; Rappoport, Z., Eds.; John Wiley and Sons: Chichester, 1988; pp 1-119.
  2. Diwu, Z.; Beachdel, C.; Klaubert, D. H. Tetrahedron Lett. 1998,39, 4987. https://doi.org/10.1016/S0040-4039(98)00975-7
  3. King, L. C.; Ostrum, G. K. J. Org. Chem. 1964, 29, 3459. https://doi.org/10.1021/jo01035a003
  4. Pasaribu, S. J.; Williams, L. R. Aust. J. Chem. 1973, 26, 1327. https://doi.org/10.1071/CH9731327
  5. Kajigaeshi, S.; Kakinami, T.; Okamoto, T.; Fujisaki, S. Bull. Chem. Soc. Jpn. 1987, 60, 1159. https://doi.org/10.1246/bcsj.60.1159
  6. Habermann, J.; Ley, S. V.; Smits, R. J. Chem. Soc., Perkin Trans. 11999, 2421.
  7. Wyman, D. P.; Kaufman, P. R. J. Org. Chem. 1964, 29, 1956. https://doi.org/10.1021/jo01030a072
  8. Kosower, E. M.; Cole, W. J.; Wu, G.-S.; Cardy, D. E.; Meisters, G.J. Org. Chem. 1963, 28, 630. https://doi.org/10.1021/jo01038a007
  9. Hakimelahi, G. H.; Just, G. Tetrahedron Lett. 1979, 3643.
  10. Lambert, F. L.; Ellis, W. D.; Parry, R. J. J. Org. Chem. 1965, 30, 304. https://doi.org/10.1021/jo01012a512
  11. Bovonsombat, P.; McNelis, E. Synthesis 1993, 237.
  12. Paul, V.; Sudalai, A.; Daniel, T.; Srinivasan, K. V. Synth. Comm. 1995, 25, 2401. https://doi.org/10.1080/00397919508015443
  13. Olah, G. A.; Wang, Q.; Sandford, G.; Prakash, G. K. S. J. Org. Chem. 1993, 58, 3194. https://doi.org/10.1021/jo00063a052

Cited by

  1. Efficient α‐Chlorination of Aryl Ketones Using Aluminum Chloride/Urea–Hydrogen Peroxide in Ionic Liquid vol.36, pp.6, 2006, https://doi.org/10.1080/00397910500449641
  2. Simple and Regioselective Bromination of 5,6-Disubstituted-indan-1-ones with Br2 Under Acidic and Basic Conditions vol.12, pp.1, 2007, https://doi.org/10.3390/12010074
  3. N-Heterocyclic Carbene Catalyzed Domino Reactions of Formylcyclopropane 1,1-Diesters: Construction of a 6-5-5 Tricyclic Pyrrolo[1,2-a]indole vol.2011, pp.3, 2010, https://doi.org/10.1002/ejoc.201001364
  4. Electrophilic Cyclizations of 2-Fluoroalk-3-yn-1-ones: Room-Temperature Synthesis of Diversely 2,5-Disubstituted 3,4-Fluorohalofurans vol.2011, pp.15, 2011, https://doi.org/10.1002/ejoc.201100344
  5. A New Solvent System (Cyclopentyl Methyl Ether–Water) in Process Development of Darifenacin HBr vol.16, pp.10, 2012, https://doi.org/10.1021/op300119s
  6. Synthesis of Substituted Furans through Domino Aldol/Homo-Michael Reactions of Formylcyclopropane 1,1-Diesters with 1,3-Dicarbonyls vol.2012, pp.13, 2012, https://doi.org/10.1002/ejoc.201200162
  7. -Bromosuccinimide vol.42, pp.18, 2012, https://doi.org/10.1080/00397911.2011.566461
  8. Structure-Based Design of Novel Potent Protein Kinase CK2 (CK2) Inhibitors with Phenyl-azole Scaffolds vol.55, pp.6, 2012, https://doi.org/10.1021/jm2015167
  9. -aminothiophenol and its derivatives as versatile synthons vol.35, pp.5, 2014, https://doi.org/10.1080/17415993.2014.934245
  10. The α-Chlorination of Aryl Methyl Ketones under Aerobic Oxidative Conditions vol.356, pp.6, 2014, https://doi.org/10.1002/adsc.201301012
  11. ]pyrimidines vol.51, pp.S1, 2014, https://doi.org/10.1002/jhet.1937
  12. Expanding the Scope of Alcohol Dehydrogenases towards Bulkier Substrates: Stereo- and Enantiopreference for α,α-Dihalogenated Ketones vol.6, pp.4, 2014, https://doi.org/10.1002/cctc.201300834
  13. Folic Acid-Conjugated Europium Complexes as Luminescent Probes for Selective Targeting of Cancer Cells vol.58, pp.4, 2015, https://doi.org/10.1021/jm501945w
  14. Use of Bromine and Bromo-Organic Compounds in Organic Synthesis vol.116, pp.12, 2016, https://doi.org/10.1021/acs.chemrev.5b00400
  15. The Role of Ligand Topology in the Decomplexation of Luminescent Lanthanide Complexes by Dipicolinic Acid vol.17, pp.20, 2016, https://doi.org/10.1002/cphc.201600727
  16. Systematic Synthesis of Diphenyl-Substituted Carotenoids as Molecular Wires vol.2017, pp.43, 2017, https://doi.org/10.1002/ejoc.201701229
  17. α,α-Alkylation-Halogenation and Dihalogenation of Sulfoxonium Ylides. A Direct Preparation of Geminal Difunctionalized Ketones vol.23, pp.67, 2017, https://doi.org/10.1002/chem.201704609
  18. Green Synthesis of (R)-Terbutaline for Recyclable Catalytic Asymmetric Transfer Hydrogenation in Ionic Liquids vol.65, pp.4, 2017, https://doi.org/10.1248/cpb.c16-00949
  19. Synthesis and antifungal activity of novel oxazolidin-2-one-linked 1,2,3-triazole derivatives vol.8, pp.12, 2017, https://doi.org/10.1039/C7MD00442G
  20. ) vol.41, pp.4, 2012, https://doi.org/10.1246/cl.2012.432
  21. Efficient Luminescence from Fluorene- and Spirobifluorene-Based Lanthanide Complexes upon Near-Visible Irradiation vol.20, pp.16, 2014, https://doi.org/10.1002/chem.201305029
  22. Iridium-Catalyzed Asymmetric Hydrogenation of Halogenated Ketones for the Efficient Construction of Chiral Halohydrins vol.360, pp.11, 2018, https://doi.org/10.1002/adsc.201800267
  23. Microwave-assisted “green” synthesis of 2-alkyl/arylbenzothiazoles in one pot: A facile approach to anti-tumor drugs vol.43, pp.6, 2006, https://doi.org/10.1002/jhet.5570430627
  24. Synthesis of various cyclopropyl methyl bromide and its derivatives from ketones and/or aldehydes and some β-dicarbonyl compounds in the presence of BrCN and Et3N pp.1735-2428, 2019, https://doi.org/10.1007/s13738-019-01600-x
  25. Efficient α-Halogenation of Carbonyl Compounds by N-Bromosuccinimide and N-Chlorosuccinimde. vol.34, pp.34, 2003, https://doi.org/10.1002/chin.200334069
  26. Efficient microwave induced direct α-halogenation of carbonyl compounds vol.45, pp.1, 2003, https://doi.org/10.1016/j.tetlet.2003.10.133
  27. TMS·OTf-Catalyzed α-bromination of carbonyl compounds by N-bromosuccinimide vol.47, pp.3, 2003, https://doi.org/10.1016/j.tetlet.2005.11.023
  28. Highly homogeneous, transparent and luminescent SiO2glassy layers containing a covalently bound tetraazacyclododecane-triacetic acid-Eu(iii)-acetophenone complex vol.16, pp.8, 2003, https://doi.org/10.1039/b514409d
  29. Efficient α-Chlorination and α-Bromination of Carbonyl Compounds Using N-Halosuccinimides/UHP in Ionic Liquid vol.37, pp.1, 2007, https://doi.org/10.1080/00397910600978168
  30. One-pot synthesis of 2-aminothiazoles in PEG-400 vol.21, pp.4, 2003, https://doi.org/10.1016/j.cclet.2009.11.035
  31. Direct synthesis of α-bromoketones from alkylarenes by aerobic visible light photooxidation vol.8, pp.20, 2010, https://doi.org/10.1039/c0ob00101e
  32. Tuning of the Electronic Properties of a Cyclopentadienylruthenium Catalyst to Match Racemization of Electron‐Rich and Electron‐Deficient Alcohols vol.17, pp.40, 2011, https://doi.org/10.1002/chem.201100827
  33. Bromination of Enamines from Tertiary Amides Using the Petasis Reagent: A Convenient One-Pot Regioselective Route to Bromomethyl Ketones vol.43, pp.21, 2003, https://doi.org/10.1080/00397911.2013.765484
  34. Ultrasound and deep eutectic solvent (DES): A novel blend of techniques for rapid and energy efficient synthesis of oxazoles vol.20, pp.1, 2013, https://doi.org/10.1016/j.ultsonch.2012.06.003
  35. Comparative material study and synthesis of 4-(4-nitrophenyl)oxazol-2-amine via sonochemical and thermal method vol.20, pp.2, 2003, https://doi.org/10.1016/j.ultsonch.2012.09.002
  36. A highly sensitive luminescent lectin sensor based on an α-D-mannose substituted Tb3+ antenna complex vol.42, pp.26, 2013, https://doi.org/10.1039/c3dt33023k
  37. Trihaloisocyanuric Acids as Atom‐Economic Reagents for Halogenation of Aromatics and Carbonyl Compounds in the Solid State by Ball Milling vol.2015, pp.12, 2015, https://doi.org/10.1002/ejoc.201403463
  38. Heterocyclic Analogs of 5,12-Naphthacenequinone 14*. Synthesis of naphtho[2,3-f]indole-3-carboxylic Acid Derivatives vol.53, pp.10, 2003, https://doi.org/10.1007/s10593-017-2173-y
  39. A Facile Synthesis of Oxiranes Possessing Three or Four Carbonyl Groups vol.23, pp.1, 2003, https://doi.org/10.2174/1385272823666190112103813
  40. Microwave‐Assisted Nanocatalysed Synthesis of Phenacyl Halides as Future Anti‐Platelet Agents vol.4, pp.32, 2003, https://doi.org/10.1002/slct.201901416
  41. One-pot synthesis of β-O-4 lignin models via the insertion of stable 2-diazo-1,3-dicarbonyls into O-H bonds vol.18, pp.25, 2003, https://doi.org/10.1039/d0ob00800a
  42. A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions vol.32, pp.1, 2003, https://doi.org/10.1016/j.cclet.2020.02.022
  43. Critical Ligand and Salt Effects in Organomagnesiate‐Promoted 3,3‐Disubstituted Phthalides Synthesis from 2‐Iodobenzoate Derivatives vol.2021, pp.34, 2003, https://doi.org/10.1002/ejoc.202100899
  44. Selenium Dioxide-Mediated Bromination of α,β-Unsaturated Ketones Using N-Bromosuccinimide in the Presence of p-Toluenesulfonic Acid: A Versatile Route for the Synthesis of α′-Br vol.6, pp.41, 2003, https://doi.org/10.1021/acsomega.1c04352
  45. Redesigning of the cap conformation and symmetry of the diphenylethyne core to yield highly potent pan-genotypic NS5A inhibitors with high potency and high resistance barrier vol.229, pp.None, 2003, https://doi.org/10.1016/j.ejmech.2021.114034
  46. Design, synthesis and biological evaluation of new imidazo[1,2-a]pyridine derivatives as selective COX-2 inhibitors vol.1250, pp.p2, 2022, https://doi.org/10.1016/j.molstruc.2021.131652