title: 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.
authors: Department of Chemistry, Indian Institute of Technology, Ropar (IIT Ropar), Nangal Road, Rupnagar, Punjab 140001, India. agoswami@iitrpr.ac.in.
authors: Nachiketa
authors: N
authors: Chatterjee
authors: Divya
authors: D
authors: Bhatt
authors: Avijit
authors: A
authors: Goswami
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D001974:Bromosuccinimide / Q000737:chemistry; D007462:Iodobenzenes / Q000737:chemistry*; D015394:Molecular Structure; D009578:Nitrobenzenes / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D012977:Sodium Nitrite / Q000737:chemistry; D013696:Temperature; D014269:Trifluoroacetic Acid / Q000737:chemistry*
chemical_list: D001897:Boronic Acids; D007462:Iodobenzenes; D009578:Nitrobenzenes; C517666:phenyliodine(III) bis(trifluoroacetate); D014269:Trifluoroacetic Acid; D001974:Bromosuccinimide; D012977:Sodium Nitrite