title: Oxygenation of Organoboronic Acids by a Nonheme Iron(II) Complex: Mimicking Boronic Acid Monooxygenase Activity.
abstract: Phenolic compounds are important intermediates in the bacterial biodegradation of aromatic compounds in the soil. An Arthrobacter sp. strain has been shown to exhibit boronic acid monooxygenase activity through the conversion of different substituted phenylboronic acids to the corresponding phenols using dioxygen. While a number of methods have been reported to cleave the C-B bonds of organoboronic acids, there is no report on biomimetic iron complex exhibiting this activity using dioxygen as the oxidant. In that direction, we have investigated the reactivity of a nucleophilic iron-oxygen oxidant, generated upon oxidative decarboxylation of an iron(II)-benzilate complex [(Tp(Ph2))Fe(II)(benzilate)] (Tp(Ph2) = hydrotris(3,5-diphenyl-pyrazol-1-yl)borate), toward organoboronic acids. The oxidant converts different aryl/alkylboronic acids to the corresponding oxygenated products with the incorporation of one oxygen atom from dioxygen. This method represents an efficient protocol for the oxygenation of boronic acids with dioxygen as the terminal oxidant.
authors.affiliation: Department of Inorganic Chemistry, Indian Association for the Cultivation of Science , 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, India.
authors.forename: Sayanti
authors.initials: S
authors.lastname: Chatterjee
authors.affiliation: Department of Inorganic Chemistry, Indian Association for the Cultivation of Science , 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, India.
authors.forename: Tapan Kanti
authors.initials: TK
authors.lastname: Paine
mesh_terms: D001897:Boronic Acids / Q000737:chemistry* / Q000378:metabolism; D004789:Enzyme Activation; D005296:Ferrous Compounds / Q000737:chemistry* / Q000378:metabolism; D006899:Mixed Function Oxygenases / Q000378:metabolism*; D010100:Oxygen / Q000737:chemistry* / Q000378:metabolism
chemical_list: D001897:Boronic Acids; D005296:Ferrous Compounds; D006899:Mixed Function Oxygenases; D010100:Oxygen