Herein we report the catalytic activity of ruthenium porphyrin complexes to promote the amination of benzylic C–H bonds by aryl azides, yielding α- and β-amino esters. The catalytic methodology is also effective to synthesize two derivatives of methyl l-3-phenyllactate in order to convert one of them into the corresponding β-lactam. The catalytic experimental conditions have been optimized on the basis of a preliminary mechanistic investigation which underlines the pivotal role of the substrate concentration to maximize the reaction productivity.
Synthesis of Biologically Relevant Compounds by Ruthenium Porphyrin Catalyzed Amination of Benzylic C-H Bonds / P. Zardi, A. Caselli, P. Macchi, F. Ferretti, E. Gallo. - In: ORGANOMETALLICS. - ISSN 0276-7333. - 33:9(2014), pp. 2210-2218. [10.1021/om500064d]
Synthesis of Biologically Relevant Compounds by Ruthenium Porphyrin Catalyzed Amination of Benzylic C-H Bonds
P. ZardiPrimo
;A. CaselliSecondo
;P. Macchi;F. FerrettiPenultimo
;E. Gallo
2014
Abstract
Herein we report the catalytic activity of ruthenium porphyrin complexes to promote the amination of benzylic C–H bonds by aryl azides, yielding α- and β-amino esters. The catalytic methodology is also effective to synthesize two derivatives of methyl l-3-phenyllactate in order to convert one of them into the corresponding β-lactam. The catalytic experimental conditions have been optimized on the basis of a preliminary mechanistic investigation which underlines the pivotal role of the substrate concentration to maximize the reaction productivity.File | Dimensione | Formato | |
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