RT Journal Article
T1 Iridium(I)-Catalyzed Intramolecular Cycloisomerization of Enynes: Scope and Mechanistic Course
A1 Fernández Fernández, David
A1 Rodrigues, Catarina A. B.
A1 Calvelo Souto, Martín
A1 Gulías Costa, Moisés
A1 Mascareñas Cid, José Luis
A1 López García, Fernando
K1 Catalysis
K1 Cyclization
K1 C−H activation
K1 Hydrocarbonation
K1 Iridium
AB We report an Ir(I)-catalyzed cycloisomerization methodology that provides access to carbocyclic systems bearing exo-alkene moieties from alkynyl-equipped acyclic precursors. The method relies on the C–H activation of olefinic and (hetero)aromatic C(sp2)–H bonds, followed by an exocyclization to a tethered alkyne, and provides interesting cyclic diene products that are amenable of further elaboration. Importantly, DFT calculations suggests that, in contrast to related hydrocarbonations of alkenes in which either migratory insertions or C–C reductive eliminations have been suggested to be rate-determining, in our reactions, the energetic barrier of these steps is lower than that of the previous C–H activation
PB American Chemical Society
YR 2018
FD 2018-07-10
LK http://hdl.handle.net/10347/17408
UL http://hdl.handle.net/10347/17408
LA eng
NO Fernández, D., Rodrigues, C., Calvelo, M., Gulías, M., Mascareñas, J., & López, F. (2018). Iridium(I)-Catalyzed Intramolecular Cycloisomerization of Enynes: Scope and Mechanistic Course. ACS Catalysis, 8(8), 7397-7402. doi: 10.1021/acscatal.8b02139
NO NOTICE:  This  is  the  peer  reviewed  version  of  the  following  article: David F. Fernández, Catarina A. B. Rodrigues, Martín Calvelo, Moisés Gulías, José L. Mascareñas and Fernando López (2018), Iridium(I)-Catalyzed Intramolecular Cycloisomerization of Enynes:Scope and Mechanistic Course. ACS Catalysis, 2018, 8 (8), 7397–7402 [DOI:  10.1021/acscatal.8b02139].  This  article  may  be  used  for non-commercial  purposes  in  accordance  with American Chemical Society  Terms and  Conditions  for  self-archiving
NO This work received financial support from the Spanish MINECO (Nos. SAF2016-76689-R, CTQ2016-77047-P, and CTQ2017-84767-P, as well as an FPI fellowship to D.F.F.), the Xunta de Galicia (Nos. ED431C 2017/19 and 2015-CP082, as well as Centro Singular de Investigación de Galicia accreditation 2016-2019 ED431G/09 and predoctoral fellowship to M.C.), the ERDF, ERC (Adv. Grant No. 340055) and the Orfeo-Cinqa network (No. CTQ2016-81797-REDC). Dr. Rebeca García-Fandiño is acknowledged for helpful suggestions on DFT studies
DS Minerva
RD 23 abr 2026