Abstract:
A mild, convenient and transition metal free methodology for oxidative ipso nitration of diversely functionalized organoboronic
acids, including heteroaryl- and alkylboronic acids, has been
developed at ambient temperature using a combination of [bis-
(trifluoroacetoxy)]iodobenzene (PIFA) – N-bromosuccinimide
(NBS) and sodium nitrite as the nitro source. It is anticipated that
the reaction proceeds through in situ generation of NO2 and
O-centred organoboronic acid radicals followed by the formation
of an O–N bond via combination of the said radicals. Finally transfer of the NO2 group to the aryl moiety occurs through 1,3-aryl
migration to provide the nitroarenes.
