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Iron–Palladium Association in the Preparation of Indoles and One‐Pot Synthesis of Bis(indolyl)methanes
Author(s) -
Terrasson Vincent,
Michaux Julien,
Gaucher Anne,
Wehbe Johny,
Marque Sylvain,
Prim Damien,
Campagne JeanMarc
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700831
Subject(s) - annulation , chemistry , palladium , catalysis , alkylation , friedel–crafts reaction , lewis acids and bases , transition metal , organic chemistry , medicinal chemistry
Indoles were prepared by annulation of the parent alkynylanilines with the use of a new FeCl 3 –PdCl 2 catalytic combination. High yields were obtained by using low loadings of the transition‐metal complex (FeCl 3 –PdCl 2 : 2 and 1 mol‐%, respectively). One‐pot accesses to bis(indolyl)methanes and trisubstituted indoles through annulation/Friedel–Crafts alkylation and annulation/1,4‐Michael addition sequences, in which FeCl 3 acts both as a cooxidant and a Lewis acid are described.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)