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Synthesis of Tetrahydrodibenzofuran and Tetrahydrophenanthridinone Skeletons by Intramolecular Nucleopalladation/Oxidative Heck Cascades

Authors

  • Claudio Martínez,

    1. Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain, Fax: +34-986-818622
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  • José M. Aurrecoechea,

    1. Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco, Apartado 644, 48080 Bilbao, Spain
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  • Youssef Madich,

    1. Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco, Apartado 644, 48080 Bilbao, Spain
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    • Student on leave from Laboratoire de Chimie Bio-Organique et Macromoléculaire, Faculté des Sciences et Techniques Marrakech, Université Cadi Ayyad, BP 549, Marrakech, Morocco

  • J. Gabriel Denis,

    1. Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain, Fax: +34-986-818622
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  • Angel R. de Lera,

    1. Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain, Fax: +34-986-818622
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  • Rosana Álvarez

    1. Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain, Fax: +34-986-818622
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Errata

This article is corrected by:

  1. Errata: Synthesis of Tetrahydrodibenzofuran and Tetrahydrophenanthridinone Skeletons by Intramolecular Nucleopalladation/Oxidative Heck Cascades Volume 2012, Issue 31, 6291–6292, Article first published online: 19 September 2012

Abstract

Functionalized alkylidene-1,2,3,4-tetrahydrodibenzo[b,d]furans and -phenanthridin-6(5H)-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.

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