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

Maxime Roche, Abdallah Hamze*, Olivier Provot, Jean-Daniel Brion and Mouad Alami*

*Université Paris-Sud, CNRS, BioCIS-UMR 8076, Faculté de Pharmacie, rue J.-B. Clément, Châtenay-Malabry, F-92296, France, Email:,

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

DOI: 10.1021/jo3023268 (free Supporting Information)


A PdCl2(MeCN)2/Xphos/NaOtBu/F-benzene system enabled the coupling of sterically hindered N-tosylhydrazones featuring ortho/ortho′-substituents on the aromatic ring with various substituted aryl halides in a sealed tube. This protocol has been applied successfully to the synthesis of a xanthene derivative.

see article for more examples

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

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

Key Words


ID: J42-Y2013-0120