A novel transition metal free [bis-(trifluoroacetoxy)iodo]benzene (PIFA) mediated oxidative ipso nitration of organoboronic acids

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.