Journal of Organic Chemistry 2005-11-11

Synthesis of 2-nitro- and 2,2'-dinitrobiphenyls by means of the suzuki cross-coupling reaction.

Raquel Rodríguez González, Lucia Liguori, Alberto Martinez Carrillo, Hans-René Bjørsvik

Index: J. Org. Chem. 70 , 9591, (2005)

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Abstract

[Reaction: see text]. Mechanistic investigations and protocols for the synthesis of 2-nitrobiphenyls and 2,2'-dinitrobiphenyls are disclosed. It is revealed that obstacles appear during the transmetalation step when the phenylboronic acid is substituted with a nitro group in the 2-position, whereas when substituted in the 3- or 4-positions, the reaction follows similar patterns as found in the electrophilic substitution of nitrobenzenes, an observation that may be attributed to the elimination step of the catalytic cycle.