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Volumn 49, Issue 17, 2010, Pages 8100-8105

HBr-H2O2: A facile protocol for regioselective synthesis of bromohydrins and α-bromoketones and oxidation of benzylic/secondary alcohols to carbonyl compounds under mild aqueous conditions

Author keywords

[No Author keywords available]

Indexed keywords

AMBIENT CONDITIONS; AQUEOUS CONDITION; AQUEOUS DIOXANE; BROMOKETONES; CARBONYL COMPOUNDS; CATALYTIC AMOUNTS; GOOD YIELD; REGIOSELECTIVE SYNTHESIS; SINGLE-STEP;

EID: 77956089043     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie100492r     Document Type: Article
Times cited : (33)

References (45)
  • 1
    • 0000107277 scopus 로고
    • Marine Haloperoxidases
    • Butler, A.; Walker, J. V. Marine Haloperoxidases Chem. Rev. 1993, 93, 1937
    • (1993) Chem. Rev. , vol.93 , pp. 1937
    • Butler, A.1    Walker, J.V.2
  • 3
    • 0036748120 scopus 로고    scopus 로고
    • An Optimized Process for Formation of 2,4-Disubstituted Imidazoles from condensation of Amidines and α-Haloketones
    • Bryan, L.; Charles, K. F.; Chiu, R. F.; Hank, J. M.; Joshua, R.; Harry, T. An Optimized Process for Formation of 2,4-Disubstituted Imidazoles from condensation of Amidines and α-Haloketones Org. Process Res. Dev. 2002, 6, 682
    • (2002) Org. Process Res. Dev. , vol.6 , pp. 682
    • Bryan, L.1    Charles, K.F.2    Chiu, R.F.3    Hank, J.M.4    Joshua, R.5    Harry, T.6
  • 4
    • 0034637262 scopus 로고    scopus 로고
    • TiCl4- n -Bu4NI as a Reducing Reagent: Pinacol Coupling and Enolate Formation from α-Haloketones
    • Takayuki, T.; Saeko, I.; Hiroshiand, S.; Koichiro, O. TiCl4- n -Bu4NI as a Reducing Reagent: Pinacol Coupling and Enolate Formation from α-Haloketones J. Org. Chem. 2000, 65, 5066
    • (2000) J. Org. Chem. , vol.65 , pp. 5066
    • Takayuki, T.1    Saeko, I.2    Hiroshiand, S.3    Koichiro, O.4
  • 5
    • 0344192466 scopus 로고
    • John Wiley & Sons: New York, Coll.
    • Langman, A. W.; Dalton, D. R. Organic Syntheses; John Wiley & Sons: New York, 1988, Coll. Vol. VI, 184 - 186.
    • (1988) Organic Syntheses , vol.6 , pp. 184-186
    • Langman, A.W.1    Dalton, D.R.2
  • 6
    • 0005823223 scopus 로고
    • Bromohydrins from Olefins and N-Bromosuccinimde in water
    • Guss, C. O.; Rosenthal, R. Bromohydrins from Olefins and N-Bromosuccinimde in water J. Am. Chem. Soc. 1955, 77, 2549
    • (1955) J. Am. Chem. Soc. , vol.77 , pp. 2549
    • Guss, C.O.1    Rosenthal, R.2
  • 9
    • 0141619393 scopus 로고    scopus 로고
    • Conversion of Epoxides into Halohydrins with Elemental Halogen Catalyzed by Thiourea
    • Sharghi, H.; Eskandari, M. M. Conversion of Epoxides into Halohydrins with Elemental Halogen Catalyzed by Thiourea Tetrahedron 2003, 59, 8509
    • (2003) Tetrahedron , vol.59 , pp. 8509
    • Sharghi, H.1    Eskandari, M.M.2
  • 10
    • 0037121848 scopus 로고    scopus 로고
    • Cleavage of Epoxides into Halohydrins with Elemental Iodine and Bromine in the Presence of 2,6-bis[2-(o-aminophenoxy)methyl]-4-bromo-1-methoxybenzene (BABMB) as Catalyst
    • Niknam, K.; Nasehi, T. Cleavage of Epoxides into Halohydrins with Elemental Iodine and Bromine in the Presence of 2,6-bis[2-(o-aminophenoxy) methyl]-4-bromo-1-methoxybenzene (BABMB) as Catalyst Tetrahedron 2002, 58, 10259
    • (2002) Tetrahedron , vol.58 , pp. 10259
    • Niknam, K.1    Nasehi, T.2
  • 11
    • 0035833088 scopus 로고    scopus 로고
    • The Halogen- Mediated Opening of Epoxides in the Presence of Pyridine-Containing Acrocycles
    • Sharghi, H.; Niknam, K.; Pooyan, M. The Halogen- Mediated Opening of Epoxides in the Presence of Pyridine-Containing Acrocycles Tetrohedron 2001, 57, 6057
    • (2001) Tetrohedron , vol.57 , pp. 6057
    • Sharghi, H.1    Niknam, K.2    Pooyan, M.3
  • 12
    • 0029921901 scopus 로고    scopus 로고
    • A Facile Conversion of Epoxides to - Halohydrins with Silica Gel-Supported Lithium Halides
    • Kotsuki, H.; Shimanouchi, T. A Facile Conversion of Epoxides to - Halohydrins with Silica Gel-Supported Lithium Halides Tetrahedron Lett. 1996, 37, 1845
    • (1996) Tetrahedron Lett. , vol.37 , pp. 1845
    • Kotsuki, H.1    Shimanouchi, T.2
  • 13
    • 70350304149 scopus 로고    scopus 로고
    • Oxidative Halogenation with Green Oxidants: Oxygen and Hydrogen Peroxide
    • For a review, see
    • For a review, see Podgorsěk, A.; Zupan, M.; Iskra, J. Oxidative Halogenation with Green Oxidants: Oxygen and Hydrogen Peroxide Angew. Chem., Int. Ed. 2009, 48, 8424
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 8424
    • Podgorsěk, A.1    Zupan, M.2    Iskra, J.3
  • 14
    • 58149308185 scopus 로고    scopus 로고
    • Selective Aerobic Oxidative Dibromination of Alkenes with Aqueous HBr and Sodium Nitrite as a Catalyst
    • Podgorsěk, A.; Eissen, M.; Fleckenstein, J.; Stavber, S.; Zupan, M.; Iskra, J. Selective Aerobic Oxidative Dibromination of Alkenes with Aqueous HBr and Sodium Nitrite as a Catalyst Green Chem. 2009, 11, 120
    • (2009) Green Chem. , vol.11 , pp. 120
    • Podgorsěk, A.1    Eissen, M.2    Fleckenstein, J.3    Stavber, S.4    Zupan, M.5    Iskra, J.6
  • 19
    • 38849101797 scopus 로고    scopus 로고
    • An Alternative Method for the Regio- and Stereoselective Bromination of Alkenes, Alkynes, Toluene Derivatives and Ketones using a Bromide/Bromate Couple
    • Adimurthy, S.; Ghosh, S.; Patoliya, P. U.; Ramachandraiah, G.; Agrawal, M.; Gandhi, M. R.; Upadhyay, S. C.; Ghosh, P. K.; Ranu, B. C. An Alternative Method for the Regio- and Stereoselective Bromination of Alkenes, Alkynes, Toluene Derivatives and Ketones using a Bromide/Bromate Couple Green Chem. 2008, 10, 232
    • (2008) Green Chem. , vol.10 , pp. 232
    • Adimurthy, S.1    Ghosh, S.2    Patoliya, P.U.3    Ramachandraiah, G.4    Agrawal, M.5    Gandhi, M.R.6    Upadhyay, S.C.7    Ghosh, P.K.8    Ranu, B.C.9
  • 20
    • 60949107951 scopus 로고    scopus 로고
    • Comparative Study of the Vicinal Functionalization of Olefins with 2:1 Bromide/Bromate and Iodide/Iodate Reagents
    • Agrawal, M. K.; Adimurthy, S.; Ganguly, B.; Ghosh, P. K. Comparative Study of the Vicinal Functionalization of Olefins with 2:1 Bromide/Bromate and Iodide/Iodate Reagents Tetrahedron 2009, 65, 2791
    • (2009) Tetrahedron , vol.65 , pp. 2791
    • Agrawal, M.K.1    Adimurthy, S.2    Ganguly, B.3    Ghosh, P.K.4
  • 21
    • 63849103125 scopus 로고    scopus 로고
    • Facile One-Pot Synthesis of α-Bromoketones from Olefins using Bromide/Bromate Couple as a Nonhazardous Brominating Agent
    • Patil, R. D.; Joshi, G.; Adimurthy, S.; Ranu, B. C. Facile One-Pot Synthesis of α-Bromoketones from Olefins using Bromide/Bromate Couple as a Nonhazardous Brominating Agent Tetrahedron Lett. 2009, 50, 2529
    • (2009) Tetrahedron Lett. , vol.50 , pp. 2529
    • Patil, R.D.1    Joshi, G.2    Adimurthy, S.3    Ranu, B.C.4
  • 22
    • 70350051022 scopus 로고    scopus 로고
    • Facile Preparation of Pd/Organoclay Catalysts with High Performance in Solvent-Free Aerobic Selective Oxidation of Benzyl Alcohol
    • Wang, H.; Deng, S. X.; Shen, Z. R.; Wang, J. G.; Ding, D. T.; Chen, T. H. Facile Preparation of Pd/Organoclay Catalysts with High Performance in Solvent-Free Aerobic Selective Oxidation of Benzyl Alcohol Green Chem. 2009, 11, 1499
    • (2009) Green Chem. , vol.11 , pp. 1499
    • Wang, H.1    Deng, S.X.2    Shen, Z.R.3    Wang, J.G.4    Ding, D.T.5    Chen, T.H.6
  • 23
    • 70049094613 scopus 로고    scopus 로고
    • Selective Aerobic Oxidation of Styrene to Benzaldehyde Catalyzed by Water-Soluble Palladium(II) Complex in Water
    • Feng, B.; Hou, Z.; Wang, X.; Hu, Y.; Li, H.; Qiao, Y. Selective Aerobic Oxidation of Styrene to Benzaldehyde Catalyzed by Water-Soluble Palladium(II) Complex in Water Green Chem. 2009, 11, 1446
    • (2009) Green Chem. , vol.11 , pp. 1446
    • Feng, B.1    Hou, Z.2    Wang, X.3    Hu, Y.4    Li, H.5    Qiao, Y.6
  • 24
    • 0034700210 scopus 로고    scopus 로고
    • Partial Oxidation of Alcohols in Supercritical Carbon Dioxide
    • Jenzer, G.; Sueur, D.; Mallat, T.; Baiker, A. Partial Oxidation of Alcohols in Supercritical Carbon Dioxide Chem. Commun. 2000, 2247
    • (2000) Chem. Commun. , pp. 2247
    • Jenzer, G.1    Sueur, D.2    Mallat, T.3    Baiker, A.4
  • 25
    • 46249127520 scopus 로고    scopus 로고
    • An Efficient and Reusable Carbon-Supported Platinum Catalyst for Aerobic Oxidation of Alcohols in Water
    • Ng, Y. H.; Ikeda, S.; Harada, T.; Morita, Y.; Matsumura, M. An Efficient and Reusable Carbon-Supported Platinum Catalyst for Aerobic Oxidation of Alcohols in Water Chem. Commun. 2008, 3181
    • (2008) Chem. Commun. , pp. 3181
    • Ng, Y.H.1    Ikeda, S.2    Harada, T.3    Morita, Y.4    Matsumura, M.5
  • 26
    • 33746597447 scopus 로고    scopus 로고
    • Mechanism of the Aerobic Oxidation of Alcohols by Palladium Complexes of N-Heterocyclic Carbenes
    • Nielsen, R. J.; Goddard, W. A., III. Mechanism of the Aerobic Oxidation of Alcohols by Palladium Complexes of N-Heterocyclic Carbenes J. Am. Chem. Soc. 2006, 128, 9651
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 9651
    • Nielsen, R.J.1    Goddard III, W.A.2
  • 27
    • 57549109687 scopus 로고    scopus 로고
    • Nanoparticle-Supported and Magnetically Recoverable Palladium (Pd) Catalyst: A Selective and Sustainable Oxidation Protocol with High Turnover Number
    • Polshettiwar, V.; Varma, R. S. Nanoparticle-Supported and Magnetically Recoverable Palladium (Pd) Catalyst: A Selective and Sustainable Oxidation Protocol with High Turnover Number Org. Biomol. Chem. 2009, 7, 37
    • (2009) Org. Biomol. Chem. , vol.7 , pp. 37
    • Polshettiwar, V.1    Varma, R.S.2
  • 28
    • 64149123277 scopus 로고    scopus 로고
    • Base-free Aqueous-Phase Oxidation of Non-Activated Alcohols with Molecular Oxygen on Soluble Pt Nanoparticles
    • Wang, T.; Shou, H.; Kou, Y.; Liu, H. Base-free Aqueous-Phase Oxidation of Non-Activated Alcohols with Molecular Oxygen on Soluble Pt Nanoparticles Green Chem. 2009, 11, 562
    • (2009) Green Chem. , vol.11 , pp. 562
    • Wang, T.1    Shou, H.2    Kou, Y.3    Liu, H.4
  • 29
    • 64149091658 scopus 로고    scopus 로고
    • Applications of a High Performance Platinum Nanocatalyst for the Oxidation of Alcohols in Water
    • Maity, P.; Gopinath, C. S.; Bhaduri, S.; Lahiri, G. K. Applications of a High Performance Platinum Nanocatalyst for the Oxidation of Alcohols in Water Green Chem. 2009, 11, 554
    • (2009) Green Chem. , vol.11 , pp. 554
    • Maity, P.1    Gopinath, C.S.2    Bhaduri, S.3    Lahiri, G.K.4
  • 30
    • 68949100611 scopus 로고    scopus 로고
    • Efficient Aerobic Oxidation of Alcohols using a Hydrotalcite-Supported Gold Nanoparticle Catalyst
    • Mitsudome, T.; Noujima, A.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Efficient Aerobic Oxidation of Alcohols using a Hydrotalcite-Supported Gold Nanoparticle Catalyst Adv. Synth. Catal. 2009, 351, 1890
    • (2009) Adv. Synth. Catal. , vol.351 , pp. 1890
    • Mitsudome, T.1    Noujima, A.2    Mizugaki, T.3    Jitsukawa, K.4    Kaneda, K.5
  • 33
    • 33646078107 scopus 로고    scopus 로고
    • Water-Soluble Organometallic Ruthenium(II) Complexes Supported on Dawson-Type Polyoxotungstates as Precatalysts: Selective Oxidation of Alcohols with 1 atm Molecular Oxygen
    • Kato, C. N.; Shinohara, A.; Moriya, N.; Nomiya, K. Water-Soluble Organometallic Ruthenium(II) Complexes Supported on Dawson-Type Polyoxotungstates as Precatalysts: Selective Oxidation of Alcohols with 1 atm Molecular Oxygen Catal. Commun. 2006, 7, 413
    • (2006) Catal. Commun. , vol.7 , pp. 413
    • Kato, C.N.1    Shinohara, A.2    Moriya, N.3    Nomiya, K.4
  • 34
    • 58149280111 scopus 로고    scopus 로고
    • The Mechanism of the Oxidation of Benzyl Alcohol by Iron(III) Nitrate: Conventional versus Microwave Heating
    • 2 Prepared at Room Temperature Green Chem. 2009, 11, 510
    • Iron: Dressen, M. H. C. L.; Stumpel, J. E.; van de Kruijs, B. H. P.; Meuldijk, J.; Vekemans, J. A. J. M.; Hulshof, L. A. The Mechanism of the Oxidation of Benzyl Alcohol by Iron(III) Nitrate: Conventional versus Microwave Heating Green Chem. 2009, 11, 60. Aluminum
    • (2009) Green Chem. , vol.11 , pp. 60
    • Dressen, M.H.C.L.1    Stumpel, J.E.2    Van De Kruijs, B.H.P.3    Meuldijk, J.4    Vekemans, J.A.J.M.5    Hulshof, L.A.6
  • 37
    • 0030195451 scopus 로고    scopus 로고
    • Kinetics and Mechanism of Anodic Oxidation of n-Butanol by Nickel Peroxide
    • Chen, Y. L.; Chou, T. C. Kinetics and Mechanism of Anodic Oxidation of n-Butanol by Nickel Peroxide Ind. Eng. Chem. Res. 1996, 35, 2172
    • (1996) Ind. Eng. Chem. Res. , vol.35 , pp. 2172
    • Chen, Y.L.1    Chou, T.C.2
  • 38
    • 33846231712 scopus 로고    scopus 로고
    • Promoting Effect and Role of Alkaline Earth Metal Added to Supported Ag Catalysts in the Gas-Phase Catalytic Oxidation of Benzyl Alcohol
    • Sawayama, Y.; Shibahara, H.; Ichihashi, Y.; Nishiyama, S.; Tsuruya, S. Promoting Effect and Role of Alkaline Earth Metal Added to Supported Ag Catalysts in the Gas-Phase Catalytic Oxidation of Benzyl Alcohol Ind. Eng. Chem. Res. 2006, 45, 8837
    • (2006) Ind. Eng. Chem. Res. , vol.45 , pp. 8837
    • Sawayama, Y.1    Shibahara, H.2    Ichihashi, Y.3    Nishiyama, S.4    Tsuruya, S.5
  • 39
    • 4444368002 scopus 로고    scopus 로고
    • Promotion Effect of Alkali Metal Added to Impregnated Cobalt Catalysts in the Gas-Phase Catalytic Oxidation of Benzyl Alcohol
    • Li, Y.; Nakashima, D.; Ichihashi, Y.; Nishiyama, S.; Tsuruya, S. Promotion Effect of Alkali Metal Added to Impregnated Cobalt Catalysts in the Gas-Phase Catalytic Oxidation of Benzyl Alcohol Ind. Eng. Chem. Res. 2004, 43, 6021
    • (2004) Ind. Eng. Chem. Res. , vol.43 , pp. 6021
    • Li, Y.1    Nakashima, D.2    Ichihashi, Y.3    Nishiyama, S.4    Tsuruya, S.5
  • 41
    • 70349432313 scopus 로고    scopus 로고
    • TEMPO and Carboxylic Acid Functionalized Imidazolium Salts/Sodium Nitrite: An Efficient, Reusable, Transition Metal-Free Catalytic System for Aerobic Oxidation of Alcohols
    • Miao, C. X.; He, L. N.; Wang, J. Q.; Wang, J. L. TEMPO and Carboxylic Acid Functionalized Imidazolium Salts/Sodium Nitrite: An Efficient, Reusable, Transition Metal-Free Catalytic System for Aerobic Oxidation of Alcohols Adv. Synth. Catal. 2009, 351, 2209
    • (2009) Adv. Synth. Catal. , vol.351 , pp. 2209
    • Miao, C.X.1    He, L.N.2    Wang, J.Q.3    Wang, J.L.4
  • 42
    • 76049096060 scopus 로고    scopus 로고
    • Making Full Use of the Oxidizing Equivalents in Bromate in the Selective Oxidation of Thiols, Sulfides, and Benzylic/Secondary Alcohols into Disulfides, Sulfoxides, and Aldehydes/Ketones
    • Joshi, G.; Bhadra, S.; Ghosh, S.; Agrawal, M. K.; Ganguly, B.; Adimurthy, S.; Ghosh, P. K.; Ranu, B. C. Making Full Use of the Oxidizing Equivalents in Bromate in the Selective Oxidation of Thiols, Sulfides, and Benzylic/Secondary Alcohols into Disulfides, Sulfoxides, and Aldehydes/Ketones Ind. Eng. Chem. Res. 2010, 49, 1236
    • (2010) Ind. Eng. Chem. Res. , vol.49 , pp. 1236
    • Joshi, G.1    Bhadra, S.2    Ghosh, S.3    Agrawal, M.K.4    Ganguly, B.5    Adimurthy, S.6    Ghosh, P.K.7    Ranu, B.C.8
  • 43
    • 0037424530 scopus 로고    scopus 로고
    • Mild Oxidation of Alcohols with o -Iodoxybenzoic Acid (IBX) in Water/Acetone Mixture in the Presence of - Cyclodextrin
    • Surendra, K.; Krishnaveni, N. S.; Reddy, M. A.; Nageswar, Y. V. D.; Rama Rao, K. Mild Oxidation of Alcohols with o -Iodoxybenzoic Acid (IBX) in Water/Acetone Mixture in the Presence of - Cyclodextrin J. Org. Chem. 2003, 68, 2058
    • (2003) J. Org. Chem. , vol.68 , pp. 2058
    • Surendra, K.1    Krishnaveni, N.S.2    Reddy, M.A.3    Nageswar, Y.V.D.4    Rama Rao, K.5
  • 44
    • 0038818516 scopus 로고    scopus 로고
    • Thermodynamic Properties of Benzyl Halides: Enthalpies of Formation, Strain Enthalpies, and Carbon-Halogen Bond Dissociation Enthalpies
    • Verevkin, S. P.; Krasnykh, E. L.; Wright, J. S. Thermodynamic Properties of Benzyl Halides: Enthalpies of Formation, Strain Enthalpies, and Carbon-Halogen Bond Dissociation Enthalpies Phys. Chem. Chem. Phys. 2003, 5, 2605
    • (2003) Phys. Chem. Chem. Phys. , vol.5 , pp. 2605
    • Verevkin, S.P.1    Krasnykh, E.L.2    Wright, J.S.3
  • 45
    • 33744901725 scopus 로고    scopus 로고
    • Highly Efficient and Selective Oxidation of Secondary Alcohols to Ketones under Organic Solvent and Transition Metal free Conditions
    • Jain, S. L.; Sharma, V. B.; Sain, B. Highly Efficient and Selective Oxidation of Secondary Alcohols to Ketones under Organic Solvent and Transition Metal free Conditions Tetrahedron 2006, 62, 6841
    • (2006) Tetrahedron , vol.62 , pp. 6841
    • Jain, S.L.1    Sharma, V.B.2    Sain, B.3


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