The Michael addition of indoles to alpha,beta-unsaturated ketones catalyzed by CeCl3.7H2O-NaI combination supported on silica gel

The Journal of Organic Chemistry
G BartoliE Torregiani

Abstract

Alkylation of indoles by means of the Michael addition has been the subject of a number of investigation. It is well established that regioselectivity in the additions of indoles to electron-deficient alkenes is strongly controlled by the reaction medium. In a continuation of the work on developing greener and cleaner technologies, the cerium(III) chloride heptahydrate and sodium iodide combination supported on silica gel catalyzes the alkylation of various indoles with alpha,beta-unsaturated ketones giving 3-(3-oxoalkyl)indole derivatives in good yields. The substitution on the indole nucleus occurred exclusively at the 3-position, and N-alkylation products have not been observed.

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Citations

Aug 19, 2011·Chemical Communications : Chem Comm·Takahiro NishimuraTamio Hayashi
Nov 15, 2006·Organic & Biomolecular Chemistry·Najmedin AziziMohammad R Saidi
Oct 13, 2006·Bioorganic & Medicinal Chemistry Letters·Ganesabaskaran SivaprasadNarayanasamy Mathivanan
Feb 23, 2018·Chemistry : a European Journal·Martin Breugst, Daniel von der Heiden
Jun 10, 2010·Organic & Biomolecular Chemistry·Giuseppe BartoliEnrico Marcantoni
Nov 18, 2010·Organic & Biomolecular Chemistry·Tianmin NiuYuhong Zhang
Apr 27, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Daniel WernerReiner Anwander
Apr 24, 2009·Chemical Reviews·Nuno R CandeiasAlexandre F Trindade
Oct 23, 2004·The Journal of Organic Chemistry·Marco BandiniAchille Umani-Ronchi
Mar 12, 2005·The Journal of Organic Chemistry·Maria AlfonsiFabio Marinelli

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