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Synfacts 2005(0): 0068-0068  
DOI: 10.1055/s-2005-869928
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Iron-Catalyzed Homo-Coupling of Arylmagnesium Reagents

Contributor(s): Paul Knochel, Andrei Gavryushin
G. Cahiez*, C. Chaboche, F. Mahuteau-Betzer, M. Ahr
CNRS-UCP-ESCOM, Cergy-Pontoise, France
Iron-Catalyzed Homo-Coupling of Simple and Functionalized Arylmagnesium Reagents
Org. Lett.  2005,  7:  1943-1946  
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Publication History

Publication Date:
20 July 2005 (online)

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Key words

arylmagnesium reagents - iron - catalysis

Significance

A very simple and convenient method for preparation of symmetrical biaryls and bis-heteroaryls from corresponding aryl- and hetaryl halides. Various functionalized Grignard reagents can be used in the reaction. The intra­molecular variant allows synthesizing interesting polycyclic systems.

Comment

The preparation of functionalized arylmagnesium compounds can be readily performed by using a halogen-magnesium exchange reaction (see, for example: A. Krasovskiy, P. Knochel Angew. Chem. Int. Ed. 2004, 43, 3333-3336) and references cited therein). There was still a need for a simple, cheap and reliable method for the homo-coupling of the highly functionalized aryl Grignard reagents. Use of FeCl3 as a catalyst makes it also environmentally friendly and convenient for large scale synthesis.

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