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Volumn 25, Issue 1, 2014, Pages 179-182

Silica gel catalyzed α-bromination of ketones using N-bromosuccinimide: An easy and rapid method

Author keywords

Bromination; Heterogeneous catalysis; Ketones; N bromosuccinimide (NBS); Silica gel

Indexed keywords


EID: 84892564209     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2013.09.014     Document Type: Article
Times cited : (12)

References (31)
  • 2
    • 3242790850 scopus 로고    scopus 로고
    • The chemistry of α-haloketones and their utility in heterocyclic synthesis
    • For review see
    • For review see: A.W. Erian, S.M. Sherif, and H.M. Gaber The chemistry of α-haloketones and their utility in heterocyclic synthesis Molecules 8 2003 93 865
    • (2003) Molecules , vol.8 , pp. 93-865
    • Erian, A.W.1    Sherif, S.M.2    Gaber, H.M.3
  • 3
    • 0347357688 scopus 로고
    • Selective bromination with copper (II) bromide
    • L.C. King, and G.K. Ostrum Selective bromination with copper (II) bromide J. Org. Chem. 29 1964 3459 3461
    • (1964) J. Org. Chem. , vol.29 , pp. 3459-3461
    • King, L.C.1    Ostrum, G.K.2
  • 4
    • 84971030541 scopus 로고
    • Selective bromination of substituted acetophenones with dioxan dibromide
    • S.J. Pasaribu, and L.K. Williams Selective bromination of substituted acetophenones with dioxan dibromide Aust. J. Chem. 26 1973 1327 1331
    • (1973) Aust. J. Chem. , vol.26 , pp. 1327-1331
    • Pasaribu, S.J.1    Williams, L.K.2
  • 5
    • 0000213449 scopus 로고
    • Synthesis of bromoacetyl derivatives by use of tetrabutylammonium tribromide
    • S. Kajigaeshi, T. Kakinami, T. Okamoto, and S. Fujisaki Synthesis of bromoacetyl derivatives by use of tetrabutylammonium tribromide Bull. Chem. Soc. Jpn. 60 1987 1159 1160
    • (1987) Bull. Chem. Soc. Jpn. , vol.60 , pp. 1159-1160
    • Kajigaeshi, S.1    Kakinami, T.2    Okamoto, T.3    Fujisaki, S.4
  • 7
    • 33750868275 scopus 로고    scopus 로고
    • A mild and regioselective method for α-bromination of β-Keto esters and 1, 3-diketones using bromodimethylsulfonium bromide (BDMS)
    • A.T. Khan, M.A. Ali, P. Goswami, and L.H. Choudhury A mild and regioselective method for α-bromination of β-Keto esters and 1, 3-diketones using bromodimethylsulfonium bromide (BDMS) J. Org. Chem. 71 2006 8961 8963
    • (2006) J. Org. Chem. , vol.71 , pp. 8961-8963
    • Khan, A.T.1    Ali, M.A.2    Goswami, P.3    Choudhury, L.H.4
  • 8
    • 58549109188 scopus 로고    scopus 로고
    • Ethylenebis(N-methylimidazolium) ditribromide (EBMIDTB): An efficient reagent for the monobromination of 1,3-diketones and β-ketoesters
    • R. Hosseinzadeh, M. Tajbakhsh, M. Mohadjerani, and Z. Lasemi Ethylenebis(N-methylimidazolium) ditribromide (EBMIDTB): an efficient reagent for the monobromination of 1,3-diketones and β-ketoesters Monatsh. Chem. 140 2009 57 60
    • (2009) Monatsh. Chem. , vol.140 , pp. 57-60
    • Hosseinzadeh, R.1    Tajbakhsh, M.2    Mohadjerani, M.3    Lasemi, Z.4
  • 9
    • 57149146555 scopus 로고    scopus 로고
    • Trihaloisocyanuric acids as convenient reagents for regioselective halogenation of β-dicarbonyl compounds
    • G.F. Mendonça, H.C. Sindra, L.S. de Almeida, P.M. Esteves, and M.C.S. de Mattos Trihaloisocyanuric acids as convenient reagents for regioselective halogenation of β-dicarbonyl compounds Tetrahedron Lett. 50 2009 473 475
    • (2009) Tetrahedron Lett. , vol.50 , pp. 473-475
    • Mendonça, G.F.1    Sindra, H.C.2    De Almeida, L.S.3    Esteves, P.M.4    De Mattos, M.C.S.5
  • 10
    • 60349112573 scopus 로고    scopus 로고
    • A mild, simple and efficient method for selective α-monobromination of 1,3-diketones and β-keto-esters using pyridinium bromochromate
    • Y. Sarrafi, M. Sadatshahabi, and K. Alimohammadi A mild, simple and efficient method for selective α-monobromination of 1,3-diketones and β-keto-esters using pyridinium bromochromate Chin. Chem. Lett. 20 2009 393 396
    • (2009) Chin. Chem. Lett. , vol.20 , pp. 393-396
    • Sarrafi, Y.1    Sadatshahabi, M.2    Alimohammadi, K.3
  • 12
    • 0037131155 scopus 로고    scopus 로고
    • Mild α-halogenation reactions of 1,3-dicarbonyl compounds catalyzed by Lewis acids
    • D. Yang, Y. Yan, and B. Lui Mild α-halogenation reactions of 1,3-dicarbonyl compounds catalyzed by Lewis acids J. Org. Chem. 67 2002 7429 7431
    • (2002) J. Org. Chem. , vol.67 , pp. 7429-7431
    • Yang, D.1    Yan, Y.2    Lui, B.3
  • 13
    • 1442325364 scopus 로고    scopus 로고
    • A mild and efficient procedure for α-bromination of ketones using N-bromosuccinimide catalysed by ammonium acetate
    • K. Tanemura, T. Suzuki, Y. Nishida, K. Satsumabayashi, and T. Horaguchi A mild and efficient procedure for α-bromination of ketones using N-bromosuccinimide catalysed by ammonium acetate Chem. Commun. 2004 470 471
    • (2004) Chem. Commun. , pp. 470-471
    • Tanemura, K.1    Suzuki, T.2    Nishida, Y.3    Satsumabayashi, K.4    Horaguchi, T.5
  • 14
    • 11144267793 scopus 로고    scopus 로고
    • ®-promoted efficient 2-halogenation of 1,3-keto-esters and cyclic ketones using N-halosuccinimides
    • ®-promoted efficient 2-halogenation of 1,3-keto-esters and cyclic ketones using N-halosuccinimides Tetrahedron Lett. 46 2005 623 626
    • (2005) Tetrahedron Lett. , vol.46 , pp. 623-626
    • Meshram, H.M.1    Reddy, P.N.2    Sadashiv, K.3    Yadav, J.S.4
  • 15
    • 15944384280 scopus 로고    scopus 로고
    • A simple and efficient method for α-bromination of carbonyl compounds using N-bromosuccinimide in the presence of silica-supported sodium hydrogen sulfate as a heterogeneous catalyst
    • B. Das, K. Venkateswarlu, G. Mahender, and I. Mahender A simple and efficient method for α-bromination of carbonyl compounds using N-bromosuccinimide in the presence of silica-supported sodium hydrogen sulfate as a heterogeneous catalyst Tetrahedron Lett. 46 2005 3041 3044
    • (2005) Tetrahedron Lett. , vol.46 , pp. 3041-3044
    • Das, B.1    Venkateswarlu, K.2    Mahender, G.3    Mahender, I.4
  • 16
    • 84857551422 scopus 로고    scopus 로고
    • 3 as the heterogeneous catalyst: An environmentally benevolent approach
    • 3 as the heterogeneous catalyst: an environmentally benevolent approach Synth. Commun. 42 2012 1091 1100
    • (2012) Synth. Commun. , vol.42 , pp. 1091-1100
    • Rahman, A.1    Jonnalagadda, S.B.2
  • 17
    • 33646862378 scopus 로고    scopus 로고
    • Sulfonic acid functionalized silica: A remarkably efficient heterogeneous reusable catalyst for α-monobromination of carbonyl compounds using N-bromosuccinimide
    • B. Das, K. Venkateswarlu, H. Holla, and M. Krishnaiah Sulfonic acid functionalized silica: a remarkably efficient heterogeneous reusable catalyst for α-monobromination of carbonyl compounds using N-bromosuccinimide J. Mol. Catal. 253 2006 107 111
    • (2006) J. Mol. Catal. , vol.253 , pp. 107-111
    • Das, B.1    Venkateswarlu, K.2    Holla, H.3    Krishnaiah, M.4
  • 18
    • 79451474888 scopus 로고    scopus 로고
    • Iron-catalyzed bromination of aryl azides by N-bromosuccinimide: Efficient method for the synthesis of brominated aryl azides
    • H. Jin, Z.D. Huang, C.X. Kuang, and X.K. Wang Iron-catalyzed bromination of aryl azides by N-bromosuccinimide: efficient method for the synthesis of brominated aryl azides Chin. Chem. Lett. 22 2011 310 313
    • (2011) Chin. Chem. Lett. , vol.22 , pp. 310-313
    • Jin, H.1    Huang, Z.D.2    Kuang, C.X.3    Wang, X.K.4
  • 19
    • 30344438843 scopus 로고    scopus 로고
    • A green approach for efficient α-halogenation of β-dicarbonyl compounds and cyclic ketones using N-halosuccinimides inionicliquids
    • H.M. Meshram, P.N. Reddy, K. Vishnu, K. Sadashiv, and J.S. Yadav A green approach for efficient α-halogenation of β-dicarbonyl compounds and cyclic ketones using N-halosuccinimides inionicliquids Tetrahedron Lett. 47 2006 991 995
    • (2006) Tetrahedron Lett. , vol.47 , pp. 991-995
    • Meshram, H.M.1    Reddy, P.N.2    Vishnu, K.3    Sadashiv, K.4    Yadav, J.S.5
  • 20
    • 33846383000 scopus 로고    scopus 로고
    • Photochemical α-bromination of ketones using N-bromosuccinimide: A simple, mild and efficient method
    • S.S. Arbuj, S.B. Waghmode, and A.V. Ramaswamy Photochemical α-bromination of ketones using N-bromosuccinimide: a simple, mild and efficient method Tetrahedron Lett. 48 2007 1411 1415
    • (2007) Tetrahedron Lett. , vol.48 , pp. 1411-1415
    • Arbuj, S.S.1    Waghmode, S.B.2    Ramaswamy, A.V.3
  • 21
    • 0036027744 scopus 로고    scopus 로고
    • Sonochemical bromination of acetophenones using p-toluenesulfonic acid - N-bromosuccinimide
    • M.V. Adhikari, and S.D. Samant Sonochemical bromination of acetophenones using p-toluenesulfonic acid - N-bromosuccinimide Ultrason. Sonochem. 9 2002 107 111
    • (2002) Ultrason. Sonochem. , vol.9 , pp. 107-111
    • Adhikari, M.V.1    Samant, S.D.2
  • 22
    • 42749089284 scopus 로고    scopus 로고
    • Halogenation of ketones with N-halosuccinimides under solvent-free reaction conditions
    • I. Pravst, M. Zupan, and S. Stavber Halogenation of ketones with N-halosuccinimides under solvent-free reaction conditions Tetrahedron 64 2008 5191 5199
    • (2008) Tetrahedron , vol.64 , pp. 5191-5199
    • Pravst, I.1    Zupan, M.2    Stavber, S.3
  • 23
    • 0037179198 scopus 로고    scopus 로고
    • Oxidation of thiols to disfiuldes with molecular bromine on hydrated silica gel support
    • M. Hashmat Ali, and M. McDermott Oxidation of thiols to disfiuldes with molecular bromine on hydrated silica gel support Tetrahedron Lett. 43 2002 6271 6273
    • (2002) Tetrahedron Lett. , vol.43 , pp. 6271-6273
    • Hashmat Ali, M.1    McDermott, M.2
  • 24
    • 79960233091 scopus 로고    scopus 로고
    • Bromination of 2,3-dihydrobenzobarrelene and synthesis of its mono- and dibromide derivatives: Unexpected Wagner-Meerwein rearrangement on silica gel
    • E. Selcuk, S. Mehmet Emin, S. Ertan, and D. Arif Bromination of 2,3-dihydrobenzobarrelene and synthesis of its mono- and dibromide derivatives: unexpected Wagner-Meerwein rearrangement on silica gel Turk. J. Chem. 35 2011 587 598
    • (2011) Turk. J. Chem. , vol.35 , pp. 587-598
    • Selcuk, E.1    Mehmet Emin, S.2    Ertan, S.3    Arif, D.4
  • 25
    • 77955417414 scopus 로고    scopus 로고
    • 2+- perfluorophthalocyanine-immobilized silica gel catalyst under mild reaction conditions
    • 2+-perfluorophthalocyanine-immobilized silica gel catalyst under mild reaction conditions Tetrahedron Lett. 51 2010 4415 4418
    • (2010) Tetrahedron Lett. , vol.51 , pp. 4415-4418
    • Sharma, R.K.1    Sharma, C.2
  • 26
    • 0026674893 scopus 로고
    • A new method for bromination and polybromination of carbazoles, β-carbolines and iminodibenzyls by using N-bromosuccinimide and silica gel
    • K. Smith, M. James, A.G. Mistry, M.R. Bye, and D.J. Faulkner A new method for bromination and polybromination of carbazoles, β-carbolines and iminodibenzyls by using N-bromosuccinimide and silica gel Tetrahedron 48 1992 7479 7488
    • (1992) Tetrahedron , vol.48 , pp. 7479-7488
    • Smith, K.1    James, M.2    Mistry, A.G.3    Bye, M.R.4    Faulkner, D.J.5
  • 27
    • 84857396924 scopus 로고    scopus 로고
    • One-pot regioselective synthesis of 4-bromopyrazole derivatives under solvent free conditions
    • H. Alinezhad, M. Tajbakhsh, and M. Zare One-pot regioselective synthesis of 4-bromopyrazole derivatives under solvent free conditions J. Mex. Chem. Soc. 55 2011 238 241
    • (2011) J. Mex. Chem. Soc. , vol.55 , pp. 238-241
    • Alinezhad, H.1    Tajbakhsh, M.2    Zare, M.3
  • 28
    • 84880141057 scopus 로고    scopus 로고
    • Regioselective α-bromination of aralkylketones using N-bromosuccinimide in presence of Montmorillonite K-10 clay: A simple and efficient method
    • R.B. Mohan, and N.C. Gangi Reddy Regioselective α-bromination of aralkylketones using N-bromosuccinimide in presence of Montmorillonite K-10 clay: a simple and efficient method Synth. Commun. 43 2013 2603 2614
    • (2013) Synth. Commun. , vol.43 , pp. 2603-2614
    • Mohan, R.B.1    Gangi Reddy, N.C.2
  • 29
    • 0031955865 scopus 로고    scopus 로고
    • Synthesis and antifungal activity of novel thiazole-containing triazole antifungals. II. Optically active ER-30346 and its derivatives
    • A. Tsuruoka, Y. Kaku, and H. Kakinuma et al. Synthesis and antifungal activity of novel thiazole-containing triazole antifungals. II. Optically active ER-30346 and its derivatives Chem. Pharm. Bull. 46 1998 623 630
    • (1998) Chem. Pharm. Bull. , vol.46 , pp. 623-630
    • Tsuruoka, A.1    Kaku, Y.2    Kakinuma, H.3
  • 30
    • 84986703669 scopus 로고
    • Terpenes and terpene derivatives, synthesis and olfactive properties of (-)- and rac-silphiperfol-5-en-3-ol and of some tris-nor derivatives
    • W. Peter, and B. Joachim Terpenes and terpene derivatives, synthesis and olfactive properties of (-)- and rac-silphiperfol-5-en-3-ol and of some tris-nor derivatives Liebigs Ann. Chem. 1992 1992 669 678
    • (1992) Liebigs Ann. Chem. , vol.1992 , pp. 669-678
    • Peter, W.1    Joachim, B.2
  • 31
    • 63849103125 scopus 로고    scopus 로고
    • Facile one-pot synthesis of α-bromoketones from olefins using bromide/bromate couple as a nonhazardous brominating agent
    • R.D. Patil, G. Joshi, S. Adimurthy, and B.C. Ranu Facile one-pot synthesis of α-bromoketones from olefins using bromide/bromate couple as a nonhazardous brominating agent Tetrahedron Lett. 50 2009 2529 2532
    • (2009) Tetrahedron Lett. , vol.50 , pp. 2529-2532
    • Patil, R.D.1    Joshi, G.2    Adimurthy, S.3    Ranu, B.C.4


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