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Ru-catalyzed C-H functionalization of phenylglycine derivatives: Synthesis of isoquinoline-1-carboxylates and isoindoline-1-carboxylates

AutorRuiz Morte, Sara ; Sayago, Francisco J. ; Cativiela, Carlos ; Urriolabeitia, Esteban P.
Palabras claveIsoindolines
Csingle bondH activation
Isoquinolines
Amino acids
Ru-complexes
Fecha de publicación2017
EditorElsevier
CitaciónJournal of Molecular Catalysis A: Chemical 426B: 407-418 (2017)
ResumenThe reaction of N-unprotected methylesters of phenylglycine derivatives (1a–1f) with electron-rich internal alkynes (2a–2e), catalyzed by [Ru(cymene)Cl] (10%), gives the corresponding 3,4-disubstituted isoquinoline-1-carboxylates 3 through C[sbnd]H/N[sbnd]H oxidative coupling. The C[sbnd]H bond activation step is assisted by carboxylates, and N-fluoro-2,4,6-trimethylpyridinium triflate works as the terminal oxidant. The process shows a remarkable tolerance to the presence of diverse electron-releasing and electron-attracting functional groups at the phenyl ring of the amino acid. In addition, the reaction of phenylglycine derivatives (1a–1f) with methyl acrylate (4a) catalyzed by [Ru(cymene)Cl] (10%) under the same experimental conditions, gives the corresponding 3,N-disubstituted isoindoline-1-carboxylates 5 through C[sbnd]H/N[sbnd]H coupling. Isoindolines 5 are obtained as a mixture of diastereoisomers, with moderate to high values of diastereomeric excess (up to 80%).
Versión del editorhttps://doi.org/10.1016/j.molcata.2016.06.026
URIhttp://hdl.handle.net/10261/155864
Identificadoresdoi: 10.1016/j.molcata.2016.06.026
issn: 1381-1169
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