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Title
Japanese:Selective N-Alkylation of Indoles with ﾎｱ,ﾎｲ-Unsaturated Compounds Catalyzed by a Monomeric Phosphate. 
English:Selective N-Alkylation of Indoles with ﾎｱ,ﾎｲ-Unsaturated Compounds Catalyzed by a Monomeric Phosphate. 
Author
Japanese: Hanako Sunaba, Keigo Kamata, Noritaka. Mizuno.  
English: Hanako Sunaba, Keigo Kamata, Noritaka. Mizuno.  
Language English 
Journal/Book name
Japanese:ChemCatChem 
English:ChemCatChem 
Volume, Number, Page Vol. 6    No. 8    pp. 2333-2338
Published date 2014 
Publisher
Japanese:Wiley-VCH Verlag GmbH & Co. KGaA 
English:Wiley-VCH Verlag GmbH & Co. KGaA 
Conference name
Japanese: 
English: 
Conference site
Japanese: 
English: 
DOI https://doi.org/10.1002/cctc.201402309
Abstract Catalytic N-alkylation of indoles is challenging because the N1 nitrogen atoms are inert toward electrophilic reagents. Herein, an org.-solvent-sol. alkylammonium salt of a simple monomeric phosphate ion, [PO4]3-, with a high charge d. acts as an efficient homogeneous catalyst for selective N-alkylation of indoles with ﾎｱ,ﾎｲ-unsatd. compds. For the reaction of indole with Et acrylate, the turnover no. reached up to 36 and the turnover frequency was 216 h-1; these values are the highest among those reported for base-mediated systems so far. In the presence of [PO4]3- ions, various combinations of nitrogen nucleophiles (ten examples) and ﾎｱ,ﾎｲ-unsatd. compds. (four examples) were efficiently converted to the desired N-alkylated products in high yields. NMR and IR spectroscopies showed formation of the indolyl anion through the activation of indole by the [PO4]3- ion, which plays an important role in the present N-alkylation. [on SciFinder(R)]

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