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Journal articles on the topic 'Catalyzed halogen exchange'

Author: Grafiati

Published: 4 June 2021

Last updated: 2 February 2022

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1

Nakada, Masahiro, Sei-ichi Tokumoto, and Minoru Hirota. "Fe3O4-Catalyzed Halogen-Exchange Reactions of Polyhalomethanes." Bulletin of the Chemical Society of Japan 60, no. 11 (November 1987): 3979–83. http://dx.doi.org/10.1246/bcsj.60.3979.

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2

Dorian, Andreas, Emily J. Landgreen, Hayley R. Petras, James J. Shepherd, and Florence J. Williams. "Iron‐Catalyzed Halogen Exchange of Trifluoromethyl Arenes**." Chemistry – A European Journal 27, no. 42 (June 17, 2021): 10839–43. http://dx.doi.org/10.1002/chem.202101324.

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3

Panferova, Liubov I., Vitalij V. Levin, Marina I. Struchkova, and Alexander D. Dilman. "Light-mediated copper-catalyzed phosphorus/halogen exchange in 1,1-difluoroalkylphosphonium salts." Chemical Communications 55, no. 9 (2019): 1314–17. http://dx.doi.org/10.1039/c8cc09115c.

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4

Nitelet, Antoine, and Gwilherm Evano. "A General Copper-Catalyzed Vinylic Halogen Exchange Reaction." Organic Letters 18, no. 8 (March 31, 2016): 1904–7. http://dx.doi.org/10.1021/acs.orglett.6b00678.

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5

Winberg, Karl Johan, Eskender Mume, Vladimir Tolmachev, and Stefan Sjöberg. "Radiobromination ofcloso-carboranes using palladium-catalyzed halogen exchange." Journal of Labelled Compounds and Radiopharmaceuticals 48, no. 3 (January 20, 2005): 195–202. http://dx.doi.org/10.1002/jlcr.914.

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6

Tao, Sheng, Enhui Ji, Lei Shi, Ning Liu, Liang Xu, and Bin Dai. "Copper-Catalyzed C–N Bond Exchange of N-Heterocyclic Substituents around Pyridine and Pyrimidine Cores." Synthesis 49, no. 23 (August 28, 2017): 5120–30. http://dx.doi.org/10.1055/s-0036-1590893.

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A copper-catalyzed transfer N-heteroarylation strategy using a C–N bond exchange reaction is described. This reaction accommodates a wide range of pyridine and pyrimidine rings bearing halogen atoms, which have wide utility for subsequent transformations. This method provides a direct and operationally simple approach for modifying complex molecules by the exchange of N-heterocyclic substituents.

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7

Dondoni, Alessandro, Marco Fogagnolo, Giancarlo Fantin, Alessandro Medici, and Paola Pedrini. "Masked multifunctionalization of aromatics by palladium-catalyzed halogen-oxazoline exchange." Tetrahedron Letters 27, no. 43 (January 1986): 5269–70. http://dx.doi.org/10.1016/s0040-4039(00)85187-4.

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8

Klapars, Artis, and Stephen L. Buchwald. "Copper-Catalyzed Halogen Exchange in Aryl Halides: An Aromatic Finkelstein Reaction." Journal of the American Chemical Society 124, no. 50 (December 2002): 14844–45. http://dx.doi.org/10.1021/ja028865v.

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9

Li, Feifei, Wanting Yang, Mengmeng Li, Lin Zhou, and Lin Lei. "Cationic quaternary ammonium salt-catalyzed LED-induced living radical polymerization with in situ halogen exchange." Polymer Chemistry 11, no. 23 (2020): 3876–83. http://dx.doi.org/10.1039/d0py00474j.

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Cationic quaternary ammonium salts were employed as organocatalysts for light-emitting diode (LED)-induced living radical polymerization (LRP) with the in situ halogen exchange of methacrylate monomers.

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10

Comins, Daniel L., Jason M. Nolan, and Ibrahim D. Bori. "Regioselective lithium–halogen exchange and palladium-catalyzed cross-coupling reactions of 2,4-dihaloquinolines." Tetrahedron Letters 46, no. 39 (September 2005): 6697–99. http://dx.doi.org/10.1016/j.tetlet.2005.07.137.

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11

Atefi, Farzad, Oliver B. Locos, Mathias O. Senge, and Dennis P. Arnold. "meso-iodo- and meso-iodovinylporphyrins via organopalladium porphyrins and the crystal structure of 5-iodo-10,20-diphenylporphyrin." Journal of Porphyrins and Phthalocyanines 10, no. 03 (March 2006): 176–85. http://dx.doi.org/10.1142/s1088424606000211.

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The regiospecific halogen exchange reactions of various easily accessible meso-bromoporphyrins to obtain meso-iodoporphyrins, using η1-palladioporphyrins as intermediates, have been investigated. This one-pot methodology allows the isolation of meso-iodoporphyrins in excellent yields with short reaction times. Similarly meso-(2-bromoethenyl)porphyrins can be converted to their iodoethenyl analogues. These iodoporphyrins show great potential as starting materials for various palladium catalyzed reactions. The X-ray crystal structure of 5-iodo-10,20-diphenylporphyrin has been determined.

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12

Wang, Jianping, Xiaofeng Tong, Xiaomin Xie, and Zhaoguo Zhang. "Rhodium-Catalyzed Activation of C(sp3)−X (X = Cl, Br) Bond: An Intermolecular Halogen Exchange Case." Organic Letters 12, no. 23 (December 3, 2010): 5370–73. http://dx.doi.org/10.1021/ol101995v.

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13

Iwata, Arihiro, Yutaka Toyoshima, Tsuyoshi Hayashida, Takahiko Ochi, Atsutaka Kunai, and Joji Ohshita. "PdCl2 and NiCl2-catalyzed hydrogen–halogen exchange for the convenient preparation of bromo- and iodosilanes and germanes." Journal of Organometallic Chemistry 667, no. 1-2 (February 2003): 90–95. http://dx.doi.org/10.1016/s0022-328x(02)02147-2.

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14

Masuda, Naoyuki, Shunsuke Tanba, Atsushi Sugie, Daiki Monguchi, Nagatoshi Koumura, Kohjiro Hara, and Atsunori Mori. "Stepwise Construction of Head-to-Tail-Type Oligothiophenes via Iterative Palladium-Catalyzed CH Arylation and Halogen Exchange." Organic Letters 11, no. 11 (June 4, 2009): 2297–300. http://dx.doi.org/10.1021/ol900622h.

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15

CURRIE, K. S., and G. TENNANT. "ChemInform Abstract: Lewis Acid Catalyzed Cyclization and Halogen Exchange Reactions of 1,1′ -Biphenyl-2-yl Isocyanide Dihalides." ChemInform 27, no. 13 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199613157.

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16

Gao, Dan-Ni, Yu-Lai Zhao, Jing-Yu Cai, Lin-Xi Hou, and Long-Qiang Xiao. "Reversible Chain Transfer Catalyzed Polymerization with Alkyl Iodides Generated from Alkyl Bromides by in Situ Halogen Exchange." Chinese Journal of Polymer Science 39, no. 9 (July 20, 2021): 1161–68. http://dx.doi.org/10.1007/s10118-021-2611-2.

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17

Balova, Irina A., Natalia A. Danilkina, and Anastasia I. Govdi. "5-Iodo-1H-1,2,3-triazoles as Versatile Building Blocks." Synthesis 52, no. 13 (April 14, 2020): 1874–96. http://dx.doi.org/10.1055/s-0039-1690858.

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Copper-catalyzed azide–alkyne cycloaddition is a useful tool for the synthesis of both 1,2,3-triazoles and 5-iodo-1H-1,2,3-triazoles starting from either terminal alkynes or iodoalkynes. 5-Iodotriazoles have been recognized as very useful building blocks for the synthesis of diverse 1,4,5-trisubstituted 1,2,3-triazoles. Synthetic application of 5-iodo-1,2,3-triazoles through the creation of a new C–C, C–heteroatom, or C–D(T) bond along with the application areas of both iodotriazoles and products of their modification including radiolabeled compounds are discussed.1 Introduction2 Synthetic Approaches to 5-Iodo-1H-1,2,3-triazoles3 5-Iodotriazoles in C–C Bond Formation3.1 Intermolecular C–C Cross-Coupling3.2 Intramolecular Cross-Coupling: Direct Arylation and C–I/C–I Homocoupling3.3 Other Transformations4 5-Iodotriazoles in Radiolabeling, Halogen Exchange, and Heterocoupling Reactions5 Summary

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18

Ramig, Keith, Linas V. Kudzma, Ralph A. Lessor, and Leonid A. Rozov. "Acid fluorides and 1,1-difluoroethyl methyl ethers as new organic sources of fluoride for antimony pentachloride-catalyzed halogen-exchange reactions." Journal of Fluorine Chemistry 94, no. 1 (February 1999): 1–5. http://dx.doi.org/10.1016/s0022-1139(98)00347-9.

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19

Woźnicki, Paweł, and Marek Stankevič. "Copper‐Catalyzed C−P Cross‐Coupling of (Cyclo)alkenyl/Aryl Bromides and Secondary Phosphine Oxides with in situ Halogen Exchange." European Journal of Organic Chemistry 2021, no. 24 (June 22, 2021): 3484–91. http://dx.doi.org/10.1002/ejoc.202100456.

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20

Ramig, Keith, Linas V. Kudzma, Ralph A. Lessor, and Leonid A. Rozov. "ChemInform Abstract: Acid Fluorides and 1,1-Difluoroethyl Methyl Ethers as New Organic Sources of Fluoride for Antimony Pentachloride-Catalyzed Halogen-Exchange Reactions." ChemInform 30, no. 29 (June 14, 2010): no. http://dx.doi.org/10.1002/chin.199929060.

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21

Milne, Jacqueline E., Krzysztof Jarowicki, and Philip J. Kocienski. "ChemInform Abstract: The Preparation of 6-Bromo-3,4-dihydro-2H-pyrans from Tetrahydropyran-2-ones via a Ni(0)-Catalyzed Coupling Reaction and Their Halogen-Metal Exchange to 6-Lithio-3,4-dihydro-2H-pyrans." ChemInform 33, no. 33 (May 20, 2010): no. http://dx.doi.org/10.1002/chin.200233147.

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22

Sheppard, Tom D. "Metal-catalysed halogen exchange reactions of aryl halides." Organic & Biomolecular Chemistry 7, no. 6 (2009): 1043. http://dx.doi.org/10.1039/b818155a.

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23

Filippou, Alexander Constantin, and Walter Grünleitner. "Proton-induzierte Kopplung eines tert-Butylisonitril-mit einem Phenylcarbin-Liganden am Wolfram / Proton-Induced Coupling of one tert-Butylisonitrile with one Phenylcarbyne Ligand at Tungsten." Zeitschrift für Naturforschung B 44, no. 9 (September 1, 1989): 1023–34. http://dx.doi.org/10.1515/znb-1989-0906.

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A good entry to highly substituted phenylcarbyne complexes of tungsten containing tert-butyl-isonitrile ligands is provided via Br(CO)2(pic)2W≡CC6H5 (1) (pic: γ-picoline). The first step includes the replacement of the picoline ligands in 1 by t-BuNC in refluxing CH2Cl2 to give Br(CO)2(t-BuNC)2 W≡CC6H5 (2) in high yield. Complex 2 is then transformed with excess t-BuNC in toluene at 90°C to the carbonyl free carbyne complex trans-Br(t-BuNC)4W≡CC6H5 (3). The monocarbonyl substituted analogue of 3, Br(CO)(t-BuNC)3W≡CC6H5 (4), is observed by IR spectroscopy as an intermediate of this reaction. Its preparation is achieved by the CoCl2 catalyzed decarbonylation of 2 in the presence of one equivalent of t-BuNC. trans-Br(t-BuNC)4W≡CC6H5 (3) and the analogous iodocompound trans-I(t-BuNC)4W≡CC6H5 (5) react with HX (X = Br, I) to give respectively, Br2(t-BuNC)3W[(t-Bu)HN—C≡C—C6H5] (6) and I2(t-BuNC)3W[(t-Bu)HN—C≡C—C6H5] (7) in high yield. Complexes 6 and 7 contain a 4e-donor acetylene ligand resulting from the proton induced coupling of one tert-butylisonitrile with the phenylcarbyne ligand at the tungsten center. The reaction of complex 4 with HBr leads also to the coupling product Br2(CO)(t-BuNC)2W[(t-Bu)HN—C≡C—C6H5] (8), the carbonyl containing analogue of 6, in low yield. With one equivalent of t-BuNC and TlPF6 compounds 6 and 7 are converted to the cationic complexes [Br(t-BuNC)4W[(t-Bu)HN—C≡C—C6H5]]+PF6- (9) and [I(t-BuNC)4W[(t-Bu)HN—C≡C—C6H5]]+PF6- (10) respectively. The analogous chloro compound [Cl(t-BuNC)4W[(t-Bu)HN—C≡C—C6H5]]+PF6- (11) is obtained by halogen exchange from 10 and PPN+Cl-. The composition and structure of the new complexes 3, 4, and 6—11 have been determined by elemental analyses, IR, 1H NMR, 13C NMR and mass spectra.

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24

Lowe, Phillip T., Steven L. Cobb, and David O'Hagan. "An enzymatic Finkelstein reaction: fluorinase catalyses direct halogen exchange." Organic & Biomolecular Chemistry 17, no. 32 (2019): 7493–96. http://dx.doi.org/10.1039/c9ob01625b.

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The fluorinase enzyme catalyses a direct displacement of bromide and iodide by fluoride ion from 5′-bromodeoxyadenosine and 5′-iododeoxyadenosine respectively to form 5′-fluorodeoxyadenosine in the absence of l-methionine or S-adenosyl-l-methionine.

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25

Hornera, L., and W. Rothb. "Chemie an starren Grenzflächen, 9 [1]. Eigenschaften und Verhalten Oniumgruppen-modifizierter Aerosile Einige Beispiele interpartikulärer Reaktionen/Chemistry on Rigid Interfaces, 9 [1]. Properties and Behaviour of Onium Group Modified Aerosils Some Examples of Interparticular Reactions." Zeitschrift für Naturforschung B 44, no. 1 (January 1, 1989): 83–90. http://dx.doi.org/10.1515/znb-1989-0119.

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Abstract Aerosils, Onium Groups. Interparticular "cross-linking" Aerosils with covalently linked onium group 2a-f catalyze the exchange of halogene (Finkel-stein-Reaction) and migrate in an electric field depending on the nature of the end groups and the kind of the suspension medium.Electroactive groups covalently linked with aerosil are electroreduced on mercury and lead cathodes. The possibility of an interparticular cross linking is demonstrated.

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26

Currie, Kevin S., and George Tennant. "Lewis acid catalysed cyclisation and halogen exchange reactions of 1,1′-biphenyl-2-yl isocyanide dihalides." J. Chem. Soc., Chem. Commun., no. 22 (1995): 2295–96. http://dx.doi.org/10.1039/c39950002295.

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27

Stoffelbach, Fran�ois, and Rinaldo Poli. "Al(OPri)3-catalysed halogen exchange processes of relevance to atom transfer radical polymerization: the effect depends on the metal electronic structure." Chemical Communications, no. 23 (2004): 2666. http://dx.doi.org/10.1039/b409992c.

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28

Bzowska, Agnieszka, Lucyna Magnowska, and Zygmunt Kazimierczuk. "Synthesis of 6-Aryloxy- and 6-Arylalkoxy-2-chloropurines and Their Interactions with Purine Nucleoside Phosphorylase from Escherichia coli." Zeitschrift für Naturforschung C 54, no. 12 (December 1, 1999): 1055–67. http://dx.doi.org/10.1515/znc-1999-1210.

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The phase transfer method was applied to perform the nucleophilic substitution of 2,6- dichloropurines by modified arylalkyl alcohol or phenols. Since under these conditions only the 6-halogen is exchanged, this method gives 2-chloro-6-aryloxy- and 2-chloro-6-arylalkoxypurines. 2-Chloro-6-benzylthiopurine was synthesized by alkylation of 2-chloro-6-thiopurine with benzyl bromide. The stereoisomers of 2-chloro-6-(1-phenyl-1-ethoxy)purine were obtained from R- and S-enantiomers of sec.-phenylethylalcohol and 2,6-dichloropurine. All derivatives were tested for inhibition with purified hexameric E. coli purine nucleoside phosphorylase (PNP). For analogues showing IC50 < 10 μm, the type of inhibition and inhibition constants were determined. In all cases the experimental data were best described by the mixed-type inhibition model and the uncompetitive inhibition constant, Kiu, was found to be several-fold lower than the competitive inhibition constant, Kic. This effect seems to be due to the 6-aryloxy- or 6-arylalkoxy substituent, because a natural PNP substrate adenine, as well as 2-chloroadenine, show mixed type inhibition with almost the same inhibition constants Kiu and KiC. The most potent inhibition was observed for 6-benzylthio-2-chloro-, 6-benzyloxy-2-chloro-, 2-chloro-6-(2-phenyl-l-ethoxy), 2-chloro-6-(3-phenyl-l-propoxy)- and 2-chloro-6-ethoxypurines (Kiu = 0.4, 0.6, 1.4, 1.4 and 2.2 μm, respectively). The R-stereoisomer of 2-chloro-6-(1pheny-1-ethoxy)purine has Kiu = 2.0 μm, whereas inhibition of its S counterpart is rather weak (IC50> 12 μm). More rigid (e.g. phenoxy-), non-planar (cyclohexyloxy-), or more bulky (2,4,6-trimethylphenoxy-) substituents at position 6 of the purine base gave less potent inhibitors (IC50 = 26, 56 and >100 μm, respectively). The derivatives are selective inhibitors of hexameric “high-molecular mass” PNPs because no inhibitory activity vs. trimeric Cellulomonas sp. PNP was detected. By establishing the ligand-dependent stabilization pattern of the E. coli PNP it was shown that the new derivatives, similarly as the natural purine bases, are able to form a dead-end ternary complex with the enzyme and orthophosphate. It was also shown that the derivatives are substrates in the reverse synthetic direction catalyzed by E. coli PNP

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29

Milne, Jacqueline E., Krzysztof Jarowicki, and Philip J. Kocienski. "The Preparation of 6-Bromo-3,4-dihydro-2H-pyrans from Tetrahydropyran-2-ones via a Ni(0)-catalysed Coupling Reaction and their Halogen-metal Exchange to 6-Lithio-3,4-dihydro-2H-pyrans." Synlett 2002, no. 04 (2002): 0607–9. http://dx.doi.org/10.1055/s-2002-22698.

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30

Sheppard, Tom D. "ChemInform Abstract: Metal-Catalyzed Halogen Exchange Reactions of Aryl Halides." ChemInform 40, no. 24 (June 16, 2009). http://dx.doi.org/10.1002/chin.200924242.

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31

Nitelet, Antoine, and Gwilherm Evano. "ChemInform Abstract: A General Copper-Catalyzed Vinylic Halogen Exchange Reaction." ChemInform 47, no. 33 (July 2016). http://dx.doi.org/10.1002/chin.201633071.

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32

Klapars, Artis, and Stephen L. Buchwald. "Copper-Catalyzed Halogen Exchange in Aryl Halides: An Aromatic Finkelstein Reaction." ChemInform 34, no. 17 (April 29, 2003). http://dx.doi.org/10.1002/chin.200317053.

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33

DONDONI, A., M. FOGAGNOLO, G. FANTIN, A. MEDICI, and P. PEDRINI. "ChemInform Abstract: Masked Multifunctionalization of Aromatics by Palladium-Catalyzed Halogen-Oxazoline Exchange." ChemInform 18, no. 13 (March 31, 1987). http://dx.doi.org/10.1002/chin.198713209.

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34

Comins, Daniel L., Jason M. Nolan, and Ibrahim D. Bori. "Regioselective Lithium—Halogen Exchange and Palladium-Catalyzed Cross-Coupling Reactions of 2,4-Dihaloquinolines." ChemInform 37, no. 2 (January 10, 2006). http://dx.doi.org/10.1002/chin.200602141.

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35

Tryniszewski, Michał, and Michal Barbasiewicz. "Gram-scale Preparation of Acyl Fluorides and Their Reactions with Hindered Nucleophiles." Synthesis, September 20, 2021. http://dx.doi.org/10.1055/a-1649-5460.

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A series of acyl fluorides was synthesized at 100 mmol scale using phase transfer catalyzed halogen exchange between acyl chlorides and aqueous bifluoride solution. The convenient procedure consists of vigorous stirring of the biphasic mixture at rt, followed by extraction and distillation. Isolated acyl fluorides (usually 7 g to 20 g) display excellent purity, and can be transformed into sterically hindered amides and esters, when treated with lithium amide bases and alkoxides under mild conditions.

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36

MARTINETZ, D., and K. LOHS. "ChemInform Abstract: Phase Transfer Catalyzed Exchange of Halogen by Cyanide or Thiocyanate in Bis(2-chloro-ethyl)sulfide." Chemischer Informationsdienst 17, no. 13 (April 1, 1986). http://dx.doi.org/10.1002/chin.198613143.

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37

"Cobalt-substituted chromia catalyses halogen exchange." Focus on Catalysts 2007, no. 6 (June 2007): 7. http://dx.doi.org/10.1016/s1351-4180(07)70349-5.

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