[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.
