A General Synthesis of 5-Arylnicotinates

Article abstract of DOI:10.1021/jo00200a045

Arylboronic acids have been found to couple efficiently with 5-bromonicotinates to yield 5-arylnicotinates.The reaction is considerably more sensitive to steric inhibition in the arylboronic acid component than in the pyridyl bromide 4.The dianion salt of the boronic acid is implicated as the reactive intermediate responsible for the facile coupling reaction.Pure arylboronic acids are best prepared by using triisopropyl borate as the transmetalating agent.