Inspired by the results of a previous mechanistic study, a series of mostly new non symmetric phenanthrolines were synthesized and tested as ligands in the palladium-catalyzed reductive carbonylation reaction of nitrobenzene to methyl phenylcarbamate. Very good results were obtained when the asymmetry was of electronic nature (a donating substituent in the para position of one of the two pyridinic rings and an electronwithdrawing or no substituent on the para position of the other pyridinic ring), but steric hindrance in the ortho or meta position retarded the reaction. The TOF for the modified system is the highest ever reported for any carbonylation reaction of nitroarenes.
New nonsymmetric phenanthrolines as very effective ligands in the palladium-catalyzed carbonylation of nitrobenzene / F. Ferretti, F. Ragaini, R. Lariccia, E. Gallo, S. Cenini. - In: ORGANOMETALLICS. - ISSN 0276-7333. - 29:6(2010), pp. 1465-1471.
New nonsymmetric phenanthrolines as very effective ligands in the palladium-catalyzed carbonylation of nitrobenzene
F. FerrettiPrimo
;F. RagainiSecondo
;E. GalloPenultimo
;S. CeniniUltimo
2010
Abstract
Inspired by the results of a previous mechanistic study, a series of mostly new non symmetric phenanthrolines were synthesized and tested as ligands in the palladium-catalyzed reductive carbonylation reaction of nitrobenzene to methyl phenylcarbamate. Very good results were obtained when the asymmetry was of electronic nature (a donating substituent in the para position of one of the two pyridinic rings and an electronwithdrawing or no substituent on the para position of the other pyridinic ring), but steric hindrance in the ortho or meta position retarded the reaction. The TOF for the modified system is the highest ever reported for any carbonylation reaction of nitroarenes.File | Dimensione | Formato | |
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