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Synthesis of 1,1-Diarylethylenes via Efficient Iron/Copper Co-Catalyzed Coupling of 1-Arylvinyl Halides with Grignard Reagents

Abdallah Hamze*, Jean-Daniel Brion and Mouad Alami*

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

A. Hamze, J.-D. Brion, M. Alami, Org. Lett., 2012, 14, 2782-2785.

DOI: 10.1021/ol3010112 (free Supporting Information)


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Abstract

The presence of FeCl3/CuTC enables an efficient coupling of functionalized aryl Grignard reagents and 1-arylvinyl halides to access 1,1-diarylethylenes of biological interest. This bimetallic system proved to be superior to the use of Fe or Cu catalyst alone. The synthetic utility of this protocol is illustrated in the field of steroid chemistry.

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Key Words

Vinylation, Arenes


ID: J54-Y2012-1680