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Marko Zupan - One of the best experts on this subject based on the ideXlab platform.
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electrophilic iodination of organic compounds using Elemental Iodine or iodides
Synthesis, 2008Co-Authors: Stojan Stavber, Marjan Jereb, Marko ZupanAbstract:Abstract: Synthetic methods for electrophilic iodination of organiccompounds using Elemental Iodine or various iodides are compiledin this review, and literature data for the last 10–15 years is organ-ised according to the type of organic compound. 1 Introduction2 Iodination of Aromatic Hydrocarbons2.1 Unsubstituted Aromatic Hydrocarbons2.2 Phenols and Aromatic Ethers2.3 Aromatic Amines2.4 Alkyl-Substituted Aromatic Hydrocarbons2.5 Deactivated Aromatic Hydrocarbons3 Iodination of Alkenes and Alkynes4 Iodination of Aliphatic Hydrocarbons5 Iodination of Organic Compounds Bearing an EnolisableCarbonyl Group 6 Iodination of Heteroatom-Containing Organic Compounds 6.1 Organoboron and Organometallic Compounds 6.2 Heterocyclic Compounds7 Conclusions and Perspectives Key words: iodination, Iodine, iodide 1 Introduction As the Iodine atom is an excellent leaving group, iodo-substituted organic compounds have for a long time beenrecognised as valuable synthons or precursors in organicsynthesis, above all in carbon–carbon, carbon–nitrogen orcarbon–oxygen bond formation.
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Effective and selective iodofunctionalisation of organic molecules in water using the Iodine-hydrogen peroxide tandem
Chemical communications (Cambridge England), 2004Co-Authors: Marjan Jereb, Marko Zupan, Stojan StavberAbstract:Efficient hydrogen peroxide enhanced iodofunctionalisation of ketones, 1,3-dicarbonyl derivatives and activated aromatic molecules using Elemental Iodine in water is achieved, whereas alkynes were stereoselectively converted into (E)-1,2-diiodoalkenes.
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Direct α-iodination of aryl alkyl ketones by Elemental Iodine activated by 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)
Synthesis, 2003Co-Authors: Marjan Jereb, Stojan Stavber, Marko ZupanAbstract:Selective introduction of an Iodine atom at the α-carbon-yl position in various aryl alkyl ketones was effectively achieved by reaction of target molecules with Elemental Iodine in the presence of N-F reagents. The best results were obtained by using 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (SelectfluorF-TEDA-BF 4 ) as the iodination mediator and methanol as the solvent. Despite a strongly activated aromatic ring, iodomethyl derivatives were thus exclusively obtained from the corresponding hydroxy and methoxy substituted acetophenone derivatives, 3-acetylindole and 2-acetylbenzofuran, while the α-iodo derivative was the main product in the case of iodination of 1,5,6,7-tetrahydro-4H-indol-4-one and 6,7-dihydro-1-benzothiophene-4(5H)-one.
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Direct iodination of indanone and tetralone derivatives by Elemental Iodine activated by Selectfluor™ F-TEDA-BF4
Tetrahedron, 2003Co-Authors: Marjan Jereb, Stojan Stavber, Marko ZupanAbstract:Abstract Derivatives of indan-1-one and 3,4-dihydronaphthalen-1(2H)-one bearing hydroxy or methoxy substituent on the aromatic ring were efficiently iodinated regioselectively at the α carbonyl position using Elemental Iodine activated by 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor™ F-TEDA-BF4) in methanol.
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Selective and Effective Iodination of Alkyl-substituted Benzenes with Elemental Iodine Activated by SelectfluorΤΜ F-TEDA-BF4
Synlett, 2002Co-Authors: Stojan Stavber, Petra Kralj, Marko ZupanAbstract:Selective direct introduction of an Iodine atom into alkyl-substituted benzene derivatives was effectively achieved by reaction of target molecules with Elemental Iodine in the presence of 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane his(tetrafluoroborate) (Selectfluor F-TEDA-BF 4 ). The number of Iodine atoms introduced could be modulated by the molar ratio between substrate, Iodine and F-TEDA-BF 4 .
Angela Tuzi - One of the best experts on this subject based on the ideXlab platform.
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Elemental Iodine or diphenyl diselenide in the bis trifluoroacetoxy iodo benzene mediated conversion of alkynes into 1 2 diketones
European Journal of Organic Chemistry, 2011Co-Authors: Marco Tingoli, Mauro Mazzella, Barbara Panunzi, Angela TuziAbstract:Both Elemental Iodine and diphenyl diselenides, in the presence of [bis(trifluoroacetoxy)iodo]benzene (PIFA), promote the transformation of internal alkynes into the corresponding 1,2-diketones. The reactions carried out in the presence of Iodine unfortunately did not proceed with complete conversion of the starting alkynes. On the other hand, diphenyl diselenide was more efficient and gave satisfactory transformation of the starting alkynes into 1,2-diketones in better yields. The structure of the vicinal dicarbonyl compounds were confirmed by applying a subsequent condensation reaction to construct the corresponding quinoxaline derivatives.
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Elemental Iodine or Diphenyl Diselenide in the [Bis(trifluoroacetoxy)iodo]benzene‐Mediated Conversion of Alkynes into 1,2‐Diketones
European Journal of Organic Chemistry, 2010Co-Authors: Marco Tingoli, Mauro Mazzella, Barbara Panunzi, Angela TuziAbstract:Both Elemental Iodine and diphenyl diselenides, in the presence of [bis(trifluoroacetoxy)iodo]benzene (PIFA), promote the transformation of internal alkynes into the corresponding 1,2-diketones. The reactions carried out in the presence of Iodine unfortunately did not proceed with complete conversion of the starting alkynes. On the other hand, diphenyl diselenide was more efficient and gave satisfactory transformation of the starting alkynes into 1,2-diketones in better yields. The structure of the vicinal dicarbonyl compounds were confirmed by applying a subsequent condensation reaction to construct the corresponding quinoxaline derivatives.
Stojan Stavber - One of the best experts on this subject based on the ideXlab platform.
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electrophilic iodination of organic compounds using Elemental Iodine or iodides
Synthesis, 2008Co-Authors: Stojan Stavber, Marjan Jereb, Marko ZupanAbstract:Abstract: Synthetic methods for electrophilic iodination of organiccompounds using Elemental Iodine or various iodides are compiledin this review, and literature data for the last 10–15 years is organ-ised according to the type of organic compound. 1 Introduction2 Iodination of Aromatic Hydrocarbons2.1 Unsubstituted Aromatic Hydrocarbons2.2 Phenols and Aromatic Ethers2.3 Aromatic Amines2.4 Alkyl-Substituted Aromatic Hydrocarbons2.5 Deactivated Aromatic Hydrocarbons3 Iodination of Alkenes and Alkynes4 Iodination of Aliphatic Hydrocarbons5 Iodination of Organic Compounds Bearing an EnolisableCarbonyl Group 6 Iodination of Heteroatom-Containing Organic Compounds 6.1 Organoboron and Organometallic Compounds 6.2 Heterocyclic Compounds7 Conclusions and Perspectives Key words: iodination, Iodine, iodide 1 Introduction As the Iodine atom is an excellent leaving group, iodo-substituted organic compounds have for a long time beenrecognised as valuable synthons or precursors in organicsynthesis, above all in carbon–carbon, carbon–nitrogen orcarbon–oxygen bond formation.
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Effective and selective iodofunctionalisation of organic molecules in water using the Iodine-hydrogen peroxide tandem
Chemical communications (Cambridge England), 2004Co-Authors: Marjan Jereb, Marko Zupan, Stojan StavberAbstract:Efficient hydrogen peroxide enhanced iodofunctionalisation of ketones, 1,3-dicarbonyl derivatives and activated aromatic molecules using Elemental Iodine in water is achieved, whereas alkynes were stereoselectively converted into (E)-1,2-diiodoalkenes.
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Direct α-iodination of aryl alkyl ketones by Elemental Iodine activated by 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)
Synthesis, 2003Co-Authors: Marjan Jereb, Stojan Stavber, Marko ZupanAbstract:Selective introduction of an Iodine atom at the α-carbon-yl position in various aryl alkyl ketones was effectively achieved by reaction of target molecules with Elemental Iodine in the presence of N-F reagents. The best results were obtained by using 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (SelectfluorF-TEDA-BF 4 ) as the iodination mediator and methanol as the solvent. Despite a strongly activated aromatic ring, iodomethyl derivatives were thus exclusively obtained from the corresponding hydroxy and methoxy substituted acetophenone derivatives, 3-acetylindole and 2-acetylbenzofuran, while the α-iodo derivative was the main product in the case of iodination of 1,5,6,7-tetrahydro-4H-indol-4-one and 6,7-dihydro-1-benzothiophene-4(5H)-one.
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Direct iodination of indanone and tetralone derivatives by Elemental Iodine activated by Selectfluor™ F-TEDA-BF4
Tetrahedron, 2003Co-Authors: Marjan Jereb, Stojan Stavber, Marko ZupanAbstract:Abstract Derivatives of indan-1-one and 3,4-dihydronaphthalen-1(2H)-one bearing hydroxy or methoxy substituent on the aromatic ring were efficiently iodinated regioselectively at the α carbonyl position using Elemental Iodine activated by 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor™ F-TEDA-BF4) in methanol.
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Selective and Effective Iodination of Alkyl-substituted Benzenes with Elemental Iodine Activated by SelectfluorΤΜ F-TEDA-BF4
Synlett, 2002Co-Authors: Stojan Stavber, Petra Kralj, Marko ZupanAbstract:Selective direct introduction of an Iodine atom into alkyl-substituted benzene derivatives was effectively achieved by reaction of target molecules with Elemental Iodine in the presence of 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane his(tetrafluoroborate) (Selectfluor F-TEDA-BF 4 ). The number of Iodine atoms introduced could be modulated by the molar ratio between substrate, Iodine and F-TEDA-BF 4 .
Marco Tingoli - One of the best experts on this subject based on the ideXlab platform.
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Elemental Iodine or diphenyl diselenide in the bis trifluoroacetoxy iodo benzene mediated conversion of alkynes into 1 2 diketones
European Journal of Organic Chemistry, 2011Co-Authors: Marco Tingoli, Mauro Mazzella, Barbara Panunzi, Angela TuziAbstract:Both Elemental Iodine and diphenyl diselenides, in the presence of [bis(trifluoroacetoxy)iodo]benzene (PIFA), promote the transformation of internal alkynes into the corresponding 1,2-diketones. The reactions carried out in the presence of Iodine unfortunately did not proceed with complete conversion of the starting alkynes. On the other hand, diphenyl diselenide was more efficient and gave satisfactory transformation of the starting alkynes into 1,2-diketones in better yields. The structure of the vicinal dicarbonyl compounds were confirmed by applying a subsequent condensation reaction to construct the corresponding quinoxaline derivatives.
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Elemental Iodine or Diphenyl Diselenide in the [Bis(trifluoroacetoxy)iodo]benzene‐Mediated Conversion of Alkynes into 1,2‐Diketones
European Journal of Organic Chemistry, 2010Co-Authors: Marco Tingoli, Mauro Mazzella, Barbara Panunzi, Angela TuziAbstract:Both Elemental Iodine and diphenyl diselenides, in the presence of [bis(trifluoroacetoxy)iodo]benzene (PIFA), promote the transformation of internal alkynes into the corresponding 1,2-diketones. The reactions carried out in the presence of Iodine unfortunately did not proceed with complete conversion of the starting alkynes. On the other hand, diphenyl diselenide was more efficient and gave satisfactory transformation of the starting alkynes into 1,2-diketones in better yields. The structure of the vicinal dicarbonyl compounds were confirmed by applying a subsequent condensation reaction to construct the corresponding quinoxaline derivatives.
Jhillu S. Yadav - One of the best experts on this subject based on the ideXlab platform.
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Mild and efficient method for the cleavage of cyclic and acyclic ethers by Iodine under solvent-free conditions
Tetrahedron Letters, 2005Co-Authors: Jhillu S. Yadav, Buthukuri Venkat Reddy, P. Murali Krishna Reddy, Manoj K. GuptaAbstract:Ethers undergo smooth cleavage with acyl chlorides in the presence of a catalytic amount of Elemental Iodine under extremely mild conditions to give the corresponding halo esters. This new procedure offers significant advantages such as high conversions, short reaction times and enhanced selectivity together with mild reaction conditions, which makes it an attractive strategy.
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Elemental Iodine catalyzed 4 2 cycloaddition reactions of o quinomethanes an efficient synthesis of trans fused pyrano 3 2 c benzopyrans
Journal of The Chemical Society-perkin Transactions 1, 2002Co-Authors: Jhillu S. Yadav, Basi Subba V Reddy, Venkateswara C Rao, Vishweshwar K RaoAbstract:Elemental Iodine has been utilized as an efficient catalyst for the intramolecular[4 + 2]cycloaddition of o-quinomethanes generated in situ from o-hydroxybenzaldehydes and unsaturated alcohol in the presence of trimethyl orthoformate to afford the corresponding trans-annelated pyrano[3,2-c]benzopyrans in high yields with high diastereoselectivity
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Elemental Iodine catalyzed [4 + 2] cycloaddition reactions of o-quinomethanes: an efficient synthesis of trans-fused pyrano[3,2-c]benzopyrans
Journal of the Chemical Society Perkin Transactions 1, 2002Co-Authors: Jhillu S. Yadav, Basi V. Subba Reddy, C. Venkateswara Rao, K. Vishweshwar RaoAbstract:Elemental Iodine has been utilized as an efficient catalyst for the intramolecular[4 + 2]cycloaddition of o-quinomethanes generated in situ from o-hydroxybenzaldehydes and unsaturated alcohol in the presence of trimethyl orthoformate to afford the corresponding trans-annelated pyrano[3,2-c]benzopyrans in high yields with high diastereoselectivity
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1,4-Conjugate addition of allyltrimethylsilane to α,β-unsaturated ketones
Tetrahedron Letters, 2002Co-Authors: Jhillu S. Yadav, B. V. S. Reddy, K. Sadasiv, G. SatheeshAbstract:Abstract α,β-Unsaturated ketones smoothly undergo conjugate addition with allyltrimethylsilane in the presence of a catalytic amount of Elemental Iodine under very mild and convenient conditions to afford the corresponding Michael adducts in high yields with high selectivity.
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A new and efficient synthesis of 2,2-disubstituted-3,4-dihydro-2H-1-benzopyrans
Journal of the Chemical Society Perkin Transactions 1, 2000Co-Authors: Jhillu S. Yadav, Basi V. Subba Reddy, Syed R. HashimAbstract:3,4-Dihydro-2,4-dimethoxy-2-methyl-2H-1-benzopyrans are formed in high yields by the cyclocondensation of o-hydroxybenzaldehydes with 2,2-dimethoxypropane catalysed by Elemental Iodine at room temperature.