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Volumn 40, Issue 5, 2010, Pages 647-653

Mild, efficient, and regioselective monobromination of arylamines and phenols using [BBIm]Br3 as a new reagent

Author keywords

BBIm Br3; Ionic liquid; Monobromination; Regioselective; Solvent free

Indexed keywords

1,3 DI N BUTYLIMIDAZOLIUM TRIBROMIDE; AROMATIC AMINE; IONIC LIQUID; PHENOL DERIVATIVE; UNCLASSIFIED DRUG; WATER;

EID: 76349113821     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903009430     Document Type: Article
Times cited : (14)

References (24)
  • 1
    • 0038288712 scopus 로고    scopus 로고
    • Palladium-catalyzed tetrakis(dimethylamino)ethylene-promoted reductive coupling of aryl halides
    • (a) Kuroboshi, M.; Waki, Y.; Tanaka, H. Palladium-catalyzed tetrakis(dimethylamino)ethylene-promoted reductive coupling of aryl halides. J. Org. Chem. 2003, 68, 3938;
    • (2003) J. Org. Chem. , vol.68 , pp. 3938
    • Kuroboshi, M.1    Waki, Y.2    Tanaka, H.3
  • 3
    • 0037702916 scopus 로고    scopus 로고
    • A highly efficient catalytic system for cross-coupling of aryl chlorides and bromides with malononitrile anion by palladium carbene complexes
    • (a) Gao, C.; Tao, X.; Qian, Y.; Huang, J. A highly efficient catalytic system for cross-coupling of aryl chlorides and bromides with malononitrile anion by palladium carbene complexes. Chem. Commun. 2003, 12, 1444;
    • (2003) Chem. Commun. , vol.12 , pp. 1444
    • Gao, C.1    Tao, X.2    Qian, Y.3    Huang, J.4
  • 4
    • 0141567591 scopus 로고    scopus 로고
    • Monomeric (dialkylamino)-boranes: A new and efficient boron source in palladium-catalyzed C-B bond formation with aryl halides
    • (b) Euzenat, L.; Horhant, D.; Ribourdouille, Y.; Duriez, C.; Alcaraz, G.; Vaultier, M. Monomeric (dialkylamino)-boranes: A new and efficient boron source in palladium-catalyzed C-B bond formation with aryl halides. Chem. Commun. 2003, 18, 2280.
    • (2003) Chem. Commun. , vol.18 , pp. 2280
    • Euzenat, L.1    Horhant, D.2    Ribourdouille, Y.3    Duriez, C.4    Alcaraz, G.5    Vaultier, M.6
  • 5
    • 0012177910 scopus 로고
    • Selective monobromination of aniline derivatives by use of bromine adsorbed on zeolite 5A
    • Onaka, M.; Izumi, Y. Selective monobromination of aniline derivatives by use of bromine adsorbed on zeolite 5A. Chem. Lett. 1984, 13, 2007.
    • (1984) Chem. Lett. , vol.13 , pp. 2007
    • Onaka, M.1    Izumi, Y.2
  • 7
    • 0344927811 scopus 로고    scopus 로고
    • 4-mediated selective oxidative halogen-ation of alkenes and aromatics using alkali metal halides
    • 4-mediated selective oxidative halogen-ation of alkenes and aromatics using alkali metal halides. Org. Lett. 2003, 5, 4501.
    • (2003) Org. Lett. , vol.5 , pp. 4501
    • Dewkar, G.K.1    Narina, S.V.2    Sudalai, A.3
  • 8
    • 0028024468 scopus 로고
    • Regioselective bromination of activated aromatic substrates with N-bromosuccinimide over HZSM-5
    • Paul, V.; Sudalai, A.; Daniel, T.; Srinivasan, K. V. Regioselective bromination of activated aromatic substrates with N-bromosuccinimide over HZSM-5. Tetrahedron Lett. 1994, 35, 7055.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 7055
    • Paul, V.1    Sudalai, A.2    Daniel, T.3    Srinivasan, K.V.4
  • 10
    • 33751392231 scopus 로고
    • 1,8-Diazabicyclo[5.4.0]undec-7-ene hydrobromide perbromide: A new, mild, stable, brominating agent for aromatic compounds
    • Muathen, H. A. 1,8-Diazabicyclo[5.4.0]undec-7-ene hydrobromide perbromide: A new, mild, stable, brominating agent for aromatic compounds. J. Org. Chem. 1992, 57, 2740.
    • (1992) J. Org. Chem. , vol.57 , pp. 2740
    • Muathen, H.A.1
  • 11
    • 0024467799 scopus 로고
    • Surfactant control of the ortho=para ratio in the bromination of anilines
    • Cerichelli, G.; Luchetti, L.; Mancini, G. Surfactant control of the ortho=para ratio in the bromination of anilines. Tetrahedron Lett. 1989, 30, 6209.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 6209
    • Cerichelli, G.1    Luchetti, L.2    Mancini, G.3
  • 12
    • 0027530281 scopus 로고
    • A convenient method for bromination of aromatic amines
    • Reeves, W. P.; King, R. M. A convenient method for bromination of aromatic amines. Synth. Commun. 1993, 23, 855.
    • (1993) Synth. Commun. , vol.23 , pp. 855
    • Reeves, W.P.1    King, R.M.2
  • 13
    • 0035944203 scopus 로고    scopus 로고
    • An efficient chemo-and regioselective oxidative nuclear bromination of activated aromatic compounds using lithium bromide and ceric ammonium nitrate
    • Roy, S. C.; Guin, C.; Rana, K. K.; Maiti, G. An efficient chemo-and regioselective oxidative nuclear bromination of activated aromatic compounds using lithium bromide and ceric ammonium nitrate. Tetrahedron Lett. 2001, 42, 6941.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 6941
    • Roy, S.C.1    Guin, C.2    Rana, K.K.3    Maiti, G.4
  • 14
    • 0039453757 scopus 로고    scopus 로고
    • Novel site-specific one-step bromin-ation of substituted benzenes
    • Srivastava, S. K.; Chauhan, P. M. S.; Bhaduri, A. P. Novel site-specific one-step bromin-ation of substituted benzenes. Chem. Commun. 1996, 23, 2679.
    • (1996) Chem. Commun. , vol.23 , pp. 2679
    • Srivastava, S.K.1    Chauhan, P.M.S.2    Bhaduri, A.P.3
  • 15
    • 0001398252 scopus 로고    scopus 로고
    • Stereoselective halogenations of alkenes and alkynes in ionic liquids
    • Chiappe, C.; Capraro, D.; Conte, V.; Pieraccini, D. Stereoselective halogenations of alkenes and alkynes in ionic liquids. Org. Lett. 2001, 3, 1061.
    • (2001) Org. Lett. , vol.3 , pp. 1061
    • Chiappe, C.1    Capraro, D.2    Conte, V.3    Pieraccini, D.4
  • 16
    • 34447132417 scopus 로고    scopus 로고
    • Innovations and green chemistry
    • Horvath, I. T.; Anastas, P. T. Innovations and green chemistry. Chem. Rev. 2007, 107, 2169.
    • (2007) Chem. Rev. , vol.107 , pp. 2169
    • Horvath, I.T.1    Anastas, P.T.2
  • 17
    • 19644382379 scopus 로고    scopus 로고
    • Ionic liquid as reagent: A green procedure for the regio-selective conversion of epoxides to vicinal-halohydrins using [AcMIm] X under catalyst and solvent-free conditions
    • (a) Ranu, B. C.; Banerjee, S. J. Ionic liquid as reagent: A green procedure for the regio-selective conversion of epoxides to vicinal-halohydrins using [AcMIm]X under catalyst and solvent-free conditions. J. Org. Chem. 2005, 70, 4517;
    • (2005) J. Org. Chem. , vol.70 , pp. 4517
    • Ranu, B.C.1    Banerjee, S.J.2
  • 18
    • 9344235002 scopus 로고    scopus 로고
    • Task-specific ionic liquids
    • (b) Davis, J. H. Task-specific ionic liquids. Chem. Lett. 2004, 33, 1072;
    • (2004) Chem. Lett. , vol.33 , pp. 1072
    • Davis, J.H.1
  • 19
    • 1642271331 scopus 로고    scopus 로고
    • Paradigm confirmed: The first use of ionic liquids to dramatically influence the outcome of chemical reactions
    • (c) Earle, M. J.; Katdare, S. P.; Seddon, K. R. Paradigm confirmed: The first use of ionic liquids to dramatically influence the outcome of chemical reactions. Org. Lett. 2004, 6, 707.
    • (2004) Org. Lett. , vol.6 , pp. 707
    • Earle, M.J.1    Katdare, S.P.2    Seddon, K.R.3
  • 20
    • 33745236612 scopus 로고    scopus 로고
    • 2) as reagent and solvent for highly selective bromination, thiocyanation, or iso-thiocyanation of alcohols and trimethylsilyl and tetrahydropyranyl ethers
    • 2) as reagent and solvent for highly selective bromination, thiocyanation, or iso-thiocyanation of alcohols and trimethylsilyl and tetrahydropyranyl ethers. Tetrahedron Lett. 2006, 47, 5531;
    • (2006) Tetrahedron Lett. , vol.47 , pp. 5531
    • Iranpoor, N.1    Firouzabadi, H.2    Azadi, R.3
  • 21
    • 10644229300 scopus 로고    scopus 로고
    • 3 as a new reagent for regioselective monobromination of arylamines under solvent-free conditions
    • 3 as a new reagent for regioselective monobromination of arylamines under solvent-free conditions. Synthesis 2004, 17, 2809;
    • (2004) Synthesis , vol.17 , pp. 2809
    • Le, Z.G.1    Chen, Z.C.2    Hu, Y.3    Zheng, Q.G.4
  • 22
    • 2942729965 scopus 로고    scopus 로고
    • Pentylpyridinium tribromide: A vapor pressure free room temperature ionic liquid analogue of bromine
    • (c) Salazar, J.; Dorta, R. Pentylpyridinium tribromide: A vapor pressure free room temperature ionic liquid analogue of bromine. Synlett 2004, 7, 1318;
    • (2004) Synlett , vol.7 , pp. 1318
    • Salazar, J.1    Dorta, R.2
  • 23
    • 9944236322 scopus 로고    scopus 로고
    • Highly efficient bromination of aromatic compounds using 3-methylimidazolium tribromide as reagent=solvent
    • (d) Chiappe, C.; Leandri, E.; Pieraccini, D. Highly efficient bromination of aromatic compounds using 3-methylimidazolium tribromide as reagent=solvent. Chem. Commun. 2004, 22, 2536.
    • (2004) Chem. Commun. , vol.22 , pp. 2536
    • Chiappe, C.1    Leandri, E.2    Pieraccini, D.3
  • 24
    • 58149500602 scopus 로고    scopus 로고
    • An efficient, rapid, and regioselective bromination of anilines and phenols with 1-butyl-3-methylpyridinium tribromide as a new reagent= solvent under mild conditions
    • Borikar, S. P.; Daniel, T.; Paul, V. An efficient, rapid, and regioselective bromination of anilines and phenols with 1-butyl-3- methylpyridinium tribromide as a new reagent= solvent under mild conditions. Tetrahedron Lett. 2009, 50, 1007.
    • (2009) Tetrahedron Lett. , vol.50 , pp. 1007
    • Borikar, S.P.1    Daniel, T.2    Paul, V.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.