Synthesis 2017; 49(22): 5045-5058
DOI: 10.1055/s-0036-1589068
paper
© Georg Thieme Verlag Stuttgart · New York

The Friedel–Crafts Reaction of Indoles with Michael Acceptors Catalyzed by Magnesium and Calcium Salts

Mikhail N. Feofanov
Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, 1-3, Moscow, 119991, Russian Federation   Email: beletska@org.chem.msu.ru
,
Maxim V. Anokhin
Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, 1-3, Moscow, 119991, Russian Federation   Email: beletska@org.chem.msu.ru
,
Alexei D. Averin
Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, 1-3, Moscow, 119991, Russian Federation   Email: beletska@org.chem.msu.ru
,
Irina P. Beletskaya*
Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, 1-3, Moscow, 119991, Russian Federation   Email: beletska@org.chem.msu.ru
› Author Affiliations
This work was financially supported by the RSF grant 14-23-00186.
Further Information

Publication History

Received: 29 April 2017

Accepted after revision: 12 June 2017

Publication Date:
02 August 2017 (eFirst)

Abstract

Friedel–Crafts alkylation of indole and its derivatives with a variety of electron-deficient alkenes catalyzed by Mg and Ca salts has been studied. The dependence of the results on the nature of the starting olefins, substituents on indole, and Michael acceptors, as well as on the composition of the Lewis acid is discussed. High yields of the addition products were achieved in the addition of indole to β,γ-unsaturated α-keto esters and coumarin derivatives, some nitroolefins, and arylidenemalonates. Reactions involving arylidenemalonates were found to be the most versatile and smooth, the best yields reached 92%. Among the Mg and Ca salts tested, magnesium iodide (MgI2) proved to be the most appropriate catalyst in the addition to various unsaturated carbonyl compounds, while calcium triflimide [Ca(NTf2)2] efficiently catalyzed the addition to nitroolefins.

Supporting Information

 
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