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Synthesis of Tetrahydrodibenzofuran and Tetrahydrophenanthridinone Skeletons by Intramolecular Nucleopalladation/Oxidative Heck Cascades
Author(s) -
Martínez Claudio,
Aurrecoechea José M.,
Madich Youssef,
Denis J. Gabriel,
de Lera Angel R.,
Álvarez Rosana
Publication year - 2012
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.201101297
Subject(s) - chemistry , sonogashira coupling , heck reaction , intramolecular force , oxidative phosphorylation , nucleophile , oxidative coupling of methane , combinatorial chemistry , stereochemistry , organic chemistry , palladium , catalysis , biochemistry
Abstract Functionalized alkylidene‐1,2,3,4‐tetrahydrodibenzo[ b , d ]furans and ‐phenanthridin‐6(5 H )‐ones have been synthesized regio‐ and stereoselectively from either o ‐iodophenols or ‐benzamides and alkynes by consecutive Pd‐catalyzed Sonogashira coupling and nucleophilic addition/oxidative Heck‐type coupling cascade reactions. In the case of iodobenzamide substrates, the whole sequence can be conveniently carried out without the isolation of intermediates. Maleic anhydride has been found to be useful as an additive in the Heck coupling step.