RT Journal Article
T1 Skeletal and Mechanistic Diversity  in Ir‐Catalyzed Cycloisomerizations of Allene‐Tethered Pyrroles and Indoles
A1 Arribas, Andrés
A1 Calvelo Souto, Martín
A1 Rey, Alejandro
A1 Mascareñas Cid, José Luis
A1 López, Fernando
AB Pyrroles and indoles bearing N-allenyl tethers participate in a variety of iridium-catalyzed cycloisomerization processes initiated by a C−H activation step, to deliver a diversity of synthetically relevant azaheterocyclic products. By appropriate selection of the ancillary ligand and the substitution pattern of the allene, the reactions can diverge from simple intramolecular hydrocarbonations to tandem processes involving intriguing mechanistic issues. Accordingly, a wide range of heterocyclic structures ranging from dihydro-indolizines and pyridoindoles to tetrahydroindolizines, as well as cyclopropane-fused tetrahydroindolizines can be obtained. Moreover, by using chiral ligands, these cascade processes can be carried out in an enantioselective manner. DFT studies provide insights into the underlying mechanisms and justify the observed chemo- regio- and stereoselectivities.
PB Wiley
YR 2024
FD 2024
LK http://hdl.handle.net/10347/34598
UL http://hdl.handle.net/10347/34598
LA eng
NO A. Arribas, M. Calvelo, A. Rey, J. L. Mascareñas, F. López. Skeletal and Mechanistic Diversity in Ir-Catalyzed Cycloisomerizations of Allene-Tethered Pyrroles and Indoles. Angew. Chem. Int. Ed. 2024, e202408258. https://doi.org/10.1002/anie.202408258
NO This work received financial support from Spanish grants (Grants PID2020-118579GB-I00 and PID2022-137318OB-I00 funded by MCIN/AEI, the ORFEO-CINQA network RED2022-134287-T and a predoctoral fellowship to A. A), the Xunta de Galicia (a predoctoral fellowship to A.R.), the Consellería de Cultura, Educación e Ordenación Universitaria (Grant ED431C 2021/25 and Grant ED431G 2019/03: Centro Singular de Investigación de Galicia accreditation 2023–2027, ED431G 2023/03) and the European Union (European Regional Development Fund-ERDF).
DS Minerva
RD 4 may 2026