5381-25-9Relevant articles and documents
Bacterial dioxygenase- and monooxygenase-catalysed sulfoxidation of benzo[b]thiophenes
Boyd, Derek R.,Sharma, Narain D.,McMurray, Brian,Haughey, Simon A.,Allen, Christopher C. R.,Hamilton, John T. G.,McRoberts, W. Colin,More O'Ferrall, Rory A.,Nikodinovic-Runic, Jasmina,Coulombel, Lydie A.,O'Connor, Kevin E.
scheme or table, p. 782 - 790 (2012/02/05)
Asymmetric heteroatom oxidation of benzo[b]thiophenes to yield the corresponding sulfoxides was catalysed by toluene dioxygenase (TDO), naphthalene dioxygenase (NDO) and styrene monooxygenase (SMO) enzymes present in P. putida mutant and E. coli recombinant whole cells. TDO-catalysed oxidation yielded the relatively unstable benzo[b]thiophene sulfoxide; its dimerization, followed by dehydrogenation, resulted in the isolation of stable tetracyclic sulfoxides as minor products with cis-dihydrodiols being the dominant metabolites. SMO mainly catalysed the formation of enantioenriched benzo[b]thiophene sulfoxide and 2-methyl benzo[b]thiophene sulfoxides which racemized at ambient temperature. The barriers to pyramidal sulfur inversion of 2- and 3-methyl benzo[b]thiophene sulfoxide metabolites, obtained using TDO and NDO as biocatalysts, were found to be ca.: 25-27 kcal mol-1. The absolute configurations of the benzo[b]thiophene sulfoxides were determined by ECD spectroscopy, X-ray crystallography and stereochemical correlation. A site-directed mutant E. coli strain containing an engineered form of NDO, was found to change the regioselectivity toward preferential oxidation of the thiophene ring rather than the benzene ring.
Carbonylation of Aryl Halides and Vinyl Bromides Mediated by Tetracarbonylcobalt Anion
Miura, Masahiro,Akase, Fumiaki,Shinohara, Masato,Nomura, Masakatsu
, p. 1021 - 1026 (2007/10/02)
The reaction of aryl halides (1a-g) with octacarbonyldicobalt in the presence of methyl iodide and sodium hydroxide under phase-transfer conditions was found to give a mixture of aryl methyl ketones (2a-g) and aromatic carboxylic acids (3a-h).From vinyl halides (9a-c), however, the corresponding carboxylic acids (10a-c) were obtained exclusively.