RT Journal Article
T1 Rhodium(III)-catalyzed intramolecular annulations involving amide-directed C–H activations: synthetic scope and mechanistic studies
A1 Quiñones, Noelia
A1 Seoane Fernández, Andrés
A1 García Fandiño, Rebeca
A1 Mascareñas Cid, José Luis
A1 Gulías Costa, Moisés
AB Alkyne tethered benzamides undergo rhodium(III)-catalyzed intramolecular annulations to give tricyclic isoquinoline derivatives in good yields. DFT calculations suggest that the reaction mechanism involves a migratory insertion of the alkyne into the rhodium–nitrogen bond of the rhodacycle intermediate that results from the initial C–H activation. This contrasts with the pathway proposed for intermolecular cases, which considers an insertion into the rhodium–carbon instead of the rhodium–nitrogen bond. The annulation is also effective with acrylamides; and, while anilides fail to participate in the process, naphthylamides do undergo the intramolecular annulation, albeit the chemoselectivity is different than for the intermolecular reactions
PB Royal Society of Chemistry
YR 2013
FD 2013
LK http://hdl.handle.net/10347/18488
UL http://hdl.handle.net/10347/18488
LA eng
NO Quiñones, N., Seoane, A., García-Fandiño, R., Mascareñas, J., & Gulías, M. (2013). Rhodium(iii)-catalyzed intramolecular annulations involving amide-directed C–H activations: synthetic scope and mechanistic studies. Chem. Sci., 4, 2874-2879. doi: 10.1039/c3sc51078f
DS Minerva
RD 23 abr 2026