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Pd-Catalyzed Reaction of Sterically Hindered Hydrazones with Aryl Halides: Synthesis of Tetra-Substituted Olefins Related to iso-Combretastatin A4

Etienne Brachet, Abdallah Hamze*, Jean-François Peyrat, Jean-Daniel Brion and Mouad Alami*

University Paris-Sud 11, CNRS, BioCIS UMR 8076, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, 5 rue J.-B. Clément, Châtenay-Malabry F-92296, France, Email: mouad.alamiu-psud.fr, abdallah.hamzeu-psud.fr

E. Brachet, A. Hamze, J.-F. Peyrat, J.-D. Brion, M. Alami, Org. Lett., 2010, 12, 4042-4045.

DOI: 10.1021/ol101639g (free Supporting Information)


Abstract

PdCl2(MeCN)2 in combination with dppp is an efficient catalyst for the coupling of sterically hindered N-arylsulfonylhydrazones with aryl halides providing a flexible and convergent access to tetrasubstituted olefins related to iso-combretastatin A4 in good yields.

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Synthesis of Ortho/Ortho′-Substituted 1,1-Diarylethylenes through Cross-Coupling Reactions of Sterically Encumbered Hydrazones and Aryl Halides

M. Roche, A. Hamze, O. Provot, J.-D. Brion, M. Alami, J. Org. Chem., 2013, 78, 445-454.


Key Words

Olefination


ID: J54-Y2010-2550