Synthesis 2017; 49(07): 1689-1701
DOI: 10.1055/s-0036-1588660
paper
© Georg Thieme Verlag Stuttgart · New York

Lewis Acid Catalyzed Friedel–Crafts Alkylation of Indoles and Other­ Electron-Rich Aromatic Compounds with Ethyl 2-(Diethoxyphosphoryl)acrylate and Tetraethyl Ethene-1,1-diylbis(phosphonate)

Elena A. Tarasenko
Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, GSP-1, Moscow 119991, Russian Federation   eMail: beletska@org.chem.msu.ru
,
Irina P. Beletskaya*
Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, GSP-1, Moscow 119991, Russian Federation   eMail: beletska@org.chem.msu.ru
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Publikationsverlauf

Received: 19. September 2016

Accepted after revision: 27. Oktober 2016

Publikationsdatum:
01. Dezember 2016 (online)


Abstract

Friedel–Crafts alkylation of indoles and other electron-rich aromatic compounds with ethyl 2-(diethoxyphosphoryl)acrylate and tetraethyl ethene-1,1-diylbis(phosphonate) was carried out in the presence of 5 mol% Cu(ClO4)2·6H2O/2,2′-Bipy complex as a catalyst in acetonitrile at room temperature to afford a broad series of heteroaryl- and aryl-substituted 2-(diethoxyphosphoryl)propionates and ethyl-1,1-diylbis(phosphonates) in 58–96% yield.

Supporting Information

 
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