- Diels-alder reaction of isobenzofurans/cyclopentadienones with tetrathiafulvalene: Preparation of naphthalene, fluoranthene, and fluorenone derivatives
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Diels-Alder reaction of 1,3-diarylbenzo[c]furan/cyclopentadienone with TTF followed by triflic acid mediated cleavage of the resulting adducts led to the formation of the respective 1,4-diaryl substituted naphthalenes, fluoranthenes, and fluorenones. The photophysical properties of representative diaryl-substituted hydrocarbons are also reported.
- Karunakaran, Jayachandran,Mohanakrishnan, Arasambattu K.
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supporting information
p. 966 - 970
(2018/02/23)
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- 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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- Cross-coupling of aryl/alkenyl ethers with aryl grignard reagents through nickel-catalyzed C-O activation
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The formation of a C-C bond has been achieved through the cleavage of the sp2 C-O bond of aryl/alkenyl ethers catalyzed by a nickel complex, and by using Grignard reagents as nucleophiles (see scheme). This method displays a broad substrate scope and leads to good to excellent yields of the aryl-aryl or alkenyl-aryl cross-coupling products.
- Xie, Lan-Gui,Wang, Zhong-Xia
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supporting information; experimental part
p. 4972 - 4975
(2011/06/17)
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