17024-12-3Relevant articles and documents
An Alternative Synthetic Method for Polycyclic Aromatic Iodides
Suzuki, Hitomi,Kondo, Akiko,Inouye, Masahiko,Ogawa, Takuji
, p. 121 - 122 (1986)
Polycyclic aromatic iodides 2 and 4 are prepared from readily available bromides 1 and 3 via the cooper(I)iodide-mediated halogen exchange with iodide ion in hot hexamethylphosphoric triamide.
A simple preparation of iodoarenes, iodoalkenes and iodoalkynes by reaction of organolithiums with 2,2,2-trifluoro-1-iodoethane
Blackmore, Ian J.,Boa, Andrew N.,Murray, Ernest J.,Dennis, Michael,Woodward, Simon
, p. 6671 - 6672 (1999)
Organolithium anions, generated either by deprotonation or lithium- bromine exchange, when quenched with 2,2,2-trifluoro-l-iodoethane produce cleanly the synthetically useful iodoarenes, iodoalkenes and iodoalkynes.
Alumina-Mediated π-Activation of Alkynes
Akhmetov, Vladimir,Amsharov, Konstantin,Feofanov, Mikhail,Sharapa, Dmitry I.
, p. 15420 - 15426 (2021/09/30)
The ability to induce powerful atom-economic transformation of alkynes is the key feature of carbophilic π-Lewis acids such as gold- and platinum-based catalysts. The unique catalytic activity of these compounds in electrophilic activations of alkynes is explained through relativistic effects, enabling efficient orbital overlapping with π-systems. For this reason, it is believed that noble metals are indispensable components in the catalysis of such reactions. In this study, we report that thermally activated γ-Al2O3activates enynes, diynes, and arene-ynes in a manner enabling reactions that were typically assigned to the softest π-Lewis acids, while some were known to be triggered exclusively by gold catalysts. We demonstrate the scope of these transformations and suggest a qualitative explanation of this phenomenon based on the Dewar-Chatt-Duncanson model confirmed by density functional theory calculations.
A palladium-catalyzed domino reaction as key step for the synthesis of functionalized aromatic amino acids
Stark, Tina,Suhartono, Marcel,G?bel, Michael W.,Lautens, Mark
supporting information, p. 2730 - 2734 (2014/01/06)
A variety of substituted aromatic systems are synthesized by the Catellani reaction. These are used as precursors for novel amino acids with a basic side chain. Georg Thieme Verlag Stuttgart New York.
Pseudo five-component synthesis of 2,5-di(hetero)arylthiophenes via a one-pot Sonogashira-Glaser cyclization sequence
Urselmann, Dominik,Antovic, Dragutin,Mueller, Thomas J. J.
supporting information; experimental part, p. 1499 - 1503 (2011/12/22)
Based upon a consecutive one-pot Sonogashira-Glaser coupling-cyclization sequence a variety of 2,5-di(hetero)arylthiophenes were synthesized in moderate to good yields. A single Pd/Cu-catalyst system, without further catalyst addition, and easily available, stable starting materials were used, resulting in a concise and highly efficient route for the synthesis of the title compounds. This novel pseudo five-component synthesis starting from iodo(hetero)arenes is particularly suitable as a direct access to well-defined thiophene oligomers, which are of peculiar interest in materials science.
Cobalt-catalyzed preparation of arylindium reagents from aryl and heteroaryl bromides
Adak, Laksmikanta,Yoshikai, Naohiko
experimental part, p. 7563 - 7568 (2011/11/12)
A cobalt-bathophenanthroline catalyst has been developed for the direct preparation of a variety of arylindium reagents from the corresponding aryl and heteroaryl bromides in the presence of indium metal and lithium chloride. The thus-formed arylindium reagents undergo efficient palladium-catalyzed cross-coupling reactions with aryl iodides, tolerating various functional groups including hydroxy and free amino groups.
Enantioselective organocatalytic anti-Mannich-type reaction of N-unprotected 3-substituted 2-oxindoles with aromatic N-Ts-aldimines
Cheng, Liang,Liu, Li,Jia, Han,Wang, Dong,Chen, Yong-Jun
supporting information; experimental part, p. 4650 - 4653 (2009/09/25)
(Chemical Equation Presented) The modified cinchona alkaloid-catalyzed direct Mannich-type reaction of N-unprotected 2-oxindoles with N-Ts-imine was developed to afford anti-3,3-disubstituted 2-oxindoles with vicinal chiral quaternary and tertiary carbon
AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT ELEMENT EMPLOYING THE SAME
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Page/Page column 36-37, (2010/02/13)
Provided are an aromatic amine compound represented by the following Formula (1) and an organic electroluminescent element which has at least one organic thin film layer containing the above aromatic amine derivative in the form of a single component. The organic electroluminescent element described above has a high luminescent efficiency even at a low voltage and a long life. It can emit blue light even at high temperatures. In Formula (1), Ar1 and Ar2 each represent naphthyl and the like; Ar3 to Ar6 each represent phenyl, naphthyl, phenanthryl and the like; Ar7 to Ar10 each represent 1,4-phenylene and the like; L represents a single bond and the like; provided that the conditions of (1) and/or (2) are satisfied:(1) at least one of Ar3 to Ar6 is a condensed aryl group having 10 to 50 nuclear carbon atoms and(2) at least one of Ar1 and Ar2 is a condensed aryl group having 12 to 50 nuclear carbon atoms.
Anomaly in Palladium-Catalyzed Phenylethynylation of 2,2'-Dihalobiphenyls: Formation of Alkylidenefluorenes
Dougherty, T. Kirk,Lau, Kreisler S. Y.,Hedberg, Frederick L.
, p. 5273 - 5280 (2007/10/02)
2,2'-Diiodobiphenyl and 5,5'-dinitro-2,2'-dihalobiphenyls underwent palladium-catalyzed phenylethynylation with 2 mol of phenylacetylene to yield 3-(fluoren-9-ylidene)-1,3-diphenylpropyne and 3-(3,6-dinitrofluoren-9-ylidene)-1,3-diphenylpropyne, respectively.These fluorenyl compounds exhibited well-defined splitting patterns for the fluorenyl ring protons in the 250-MHz proton NMR spectra.The structure of 3-(fluoren-9-ylidene)-1,3-diphenylpropyne was further confirmed by an independent synthesis via the thermolysis of diethyl 3-(fluoren-9-ylidene)-1,3-diphenylpropen-1-yl phosphate.The mechanistic importance of the complex iodo(fluoren-9-ylidenebenzyl)bis(triphenylphosphine)palladium(II) in the catalytic cycle was established on the basis of its reaction with phenylacetylene to give 3-(fluoren-9-ylidene)-1,3-diphenylpropyne.
