- Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles
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Various 1-methyl-, 1-triisopropylsilyl-, and 1-benzylindoles are carboxylated under CO2 pressure (3.0 MPa) with the aid of 1.0 molar equiv of Me2AlCl to give 1-substituted indole-3-carboxylic acids in good to excellent yields. Mechanistic studies suggest that the intermediate, an indol-3-ylaluminum ate complex, was reversibly formed by electrophilic addition of Me2AlCl to the substrate followed by deprotonation of the resulting adduct. This method is successfully extended to alkoxycarbonylation with ethyl chloroformate and carbamoylation with naphthalen-1-yl isocyanate, which afford ethyl indole-3-carboxylates and N-naphthalen-1-ylindole-3-carboxamides, respectively.
- Nemoto, Koji,Tanaka, Shinya,Konno, Megumi,Onozawa, Satoru,Chiba, Masafumi,Tanaka, Yuuki,Sasaki, Yosuke,Okubo, Ryo,Hattori, Tetsutaro
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p. 734 - 745
(2016/01/15)
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- Synthesis of diversely substituted indoloquinolinones via Pd(II)/Cu(II)-mediated oxidative C-C bond formation and I(III)-mediated C-N bond formation
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A series of indoloquinolinones bearing different aromatic substitutents were readily synthesized starting from an aryl amine, a methyl 3-oxo-3-phenylpropanoate derivative, and methoxylamine through a series of reactions of coupling/enamination, oxidative
- Zhang, Xiang,Zhang-Negrerie, Daisy,Deng, Jun,Du, Yunfei,Zhao, Kang
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p. 12750 - 12759
(2014/01/17)
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- Carboxylation of indoles and pyrroles with CO2 in the presence of dialkylaluminum halides
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The Lewis acid-mediated carboxylation of arenes with CO2 has been successfully applied to 1-substituted indoles and pyrroles by using dialkylaluminum chlorides instead of aluminum trihalides. Thus, the carboxylation of 1-methylindoles, 1-benzyl-, and 1-phenylpyrroles proceeds regioselectively with the aid of an equimolar amount of Me2AlCl under CO2 pressure (3.0 MPa) at room temperature to afford the corresponding indole-3-carboxylic acids and pyrrole-2-carboxylic acids in 61-85% yields, while the same treatment of 1,2,5-trimethylpyrrole affords the 3-carboxylic acid in 52% yield.
- Nemoto, Koji,Onozawa, Satoru,Egusa, Naoki,Morohashi, Naoya,Hattori, Tetsutaro
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experimental part
p. 4512 - 4514
(2009/11/30)
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- Fluorescent diarylindoles by palladium-catalyzed direct and decarboxylative arylations of carboxyindoles
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A study was conducted to demonstrate the palladium-catalyzed 2,3-diarylation of carboxyindole derivatives with acryl bromides. The study also performed ester hydrolysis in the sequence to demonstrate a practical route to 2,3-diarylindoles that had differe
- Miyasaka, Mitsuru,Fukushima, Azusa,Satoh, Tetsuya,Hirano, Koji,Miura, Masahiro
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supporting information; experimental part
p. 3674 - 3677
(2009/12/25)
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- Photocarboxylation in the Presence of Aromatic Amines and Carbon Dioxide
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Phenylethylenes (1), biphenyl, and 1-methyl-2-phenylindole underwent carboxylation upon photolysis in the presence of aromatic amines (2) and carbon dioxide.
- Ito, Yoshikatsu,Uozu, Yoshihiro,Matsuura, Teruo
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p. 562 - 564
(2007/10/02)
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