A Practical Protocol for the Hiyama Cross-Coupling Reaction Catalyzed by Palladium on Carbon

Abstract

A method for the palladium on carbon (Pd/C) catalyzed cross-coupling reaction between aryl halides and trialkoxy(aryl)silanes in the presence of a small amount of water is established using tris(4-fluorophenyl)phosphine as the ligand. A range of biaryl compounds is prepared using this protocol.

Key words

palladium - cross-coupling - heterogeneous - silicon - biaryls

• References


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In the presence of a small amount of water, the alkoxy groups of the triethoxy(aryl)silane would be hydrated into the corresponding hydroxy groups, and the electrophilicity of the silicon atom would increase. On the other hand, addition of an excess amount of water resulted in the formation of inactive caged siloxane derivatives, see reference 11 and:
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