- Sonochemical synthesis of bis(tri-n-butylstannyl) aromatic compounds via Barbier-like reactions
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This paper reports a study of the synthesis of aryltri-n-butylstannanes via a sonochemical Barbier reaction of aryl- and heteroaryl bromides with bis(tri-n-butyltin) oxide (2) in THF. Our results demonstrate that, despite previous reports on contrary, the aryltributylstannanes can also be obtained under the same reaction conditions via sonicated reactions between aryl monobromides and tri-nbutyltin chloride (2). A comparative study of the reactions of electrophiles 2 and 3 with bromobenzene, 2-bromopyridin, o- and m-bromoanisole, m-bromotoluene, 9-bromophenthrene, and 9-bromoanthracene, indicates that the corresponding aryl- and heteroaryl-tri-n-butylstannyl derivatives are obtained in about the sameyields. Best reaction conditions and the results obtained in the investigation of the sonicated reactions between several aromatic and heteroaromatic dibromides are also reported. It was found that the reactions using 1,2-, 1,3-, and 1,4-dibromobenzenes, 4,40-dibromobiphenyl, 1,4-dibromonaphthalene, 2,5-and 3,5-dibromopyridines, and 2,5-dibromothiophene lead to the corresponding bis(tri-n-butylstannylated) derivatives in many cases in very high yields. Also the excellent results obtained in the sonicated reactions of 1,3,5-tribromobenzene with 2 and 3 are reported.
- Gerbino, Darío C.,Fidelibus, Pablo M.,Mandolesi, Sandra D.,Ocampo, Romina A.,Scoccia, Jimena,Podestá, Julio C.
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- π-electron conjugated compound, manufacturing method therefor, and π-electron conjugated polymer obtained using same
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Provided are a π-electron conjugated polymer having a constitutional unit represented by general formula (2) that is suitable as an electrochromic material that changes from a desired colored state to a decolored state, a new compound that is a raw materi
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Page/Page column 36
(2013/08/28)
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- Distannylation of strained carbon-carbon triple bonds catalyzed by a palladium complex
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Oxidative addition of a distannane to a palladium(0) complex occurs during the distannylation of in situ generated arynes with distannanes in the presence of a catalytic amount of a palladium/tert-octyl isocyanide (tOcNC) complex to give 1,2-distannylarenes in moderate to high yields (see scheme). Bisarynes and cyclohexynes can also be used as substrates for the reaction.
- Yoshida, Hiroto,Tanino, Kenji,Ohshita, Joji,Kunai, Atsutaka
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p. 5052 - 5055
(2007/10/03)
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- General synthetic entry to highly-oxygenated, angularly-fused polycyclic aromatic compounds
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A convergent and efficient synthesis of highly-oxygenated, angularly-fused polycyclic aromatic compounds has been developed. Nucleophilic addition of [4-(tri-n-butylstannyl)phenyl]lithium to a 3,4-disubstituted-cyclobutene-1,2-dione followed by appropriate protection of the hydroxyl group and thermal rearrangement of the O-protected addition product generated a 1,4-dioxygenated-2,3-disubstituted-6-(tri-n-butylstannyl)naphthalene. Stille coupling of the 6-(tri-n-butylstannyl)naphthalene with a 4-chloro-2,3-disubstituted-2-cyclobutenone and thermolysis of the coupled product gave highly-oxygenated phenanthrenes. An isomeric series of compounds was generated from [3-(tri-n-butylstannyl)phenyl]lithium. Substituted phenanthrenes at higher overall levels of oxygenation were prepared by (1) thermolysis of the adduct obtained by addition of a lithiated naphthalene, generated by Sn → Li exchange from a 1,4-dioxygenated-2,3-disubstituted-6-(tri-n-butylstannyl)naphthalene, to a cyclobutenedione or (2) thermolysis of the double adducts generated by reaction of 2 equiv of a cyclobutenedione with either 1,4-dilithiobenzene or 1,3-dilithiobenzene. Phenanthrenes at lower levels of oxygenation were prepared by the palladium-catalyzed cross-coupling/thermolysis of 2 equivalents of a 4-chlorocyclobutenone with either 1,4-bis(tri-n-butylstannyl)benzene or 1,3-bis(tri-n-butylstannyl)benzene.
- Koo, Sangho,Liebeskind, Lanny S.
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p. 3389 - 3404
(2007/10/02)
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- Reaction of Arylboronic Acids and their Derivatives with Lead Tetra-acetate. The Generation of Aryl-lead Triacetates, and meta- and para-Phenylenebis(lead triacetate), in situ for Electrophilic Arylation
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Arylboronic acids and some of their derivatives have been found to undergo a rapid boron-lead exchange with lead tetra-acetate.In the presence of a catalytic amount of mercury(II) acetate, the reaction produces mainly the aryl-lead triacetate, and it has been developed as a convenient method for in situ generation of these useful electrophilic C-arylating reagents.The reaction allows the generation for the first time of meta- and para-phenylenebis(lead triacetate), compounds which behave as meta- and para-phenylene dication equivalents.
- Morgan, Jacqueline,Pinhey, John T.
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p. 715 - 720
(2007/10/02)
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