RT Journal Article
T1 Pd-Catalyzed (3 + 2) Heterocycloadditions between Alkylidenecyclopropanes and Carbonyls: Straightforward Assembly of Highly Substituted Tetrahydrofurans
A1 Verdugo Leal, Felipe Ignacio
A1 Concepción Vicente, Eduardo da
A1 Rodiño Balboa, Ricardo
A1 Calvelo Souto, Martín
A1 Mascareñas Cid, José Luis
A1 López García, Fernando
K1 Palladium
K1 Hydrocarbons
K1 Cyclization
K1 Ketones
K1 Catalysts
K1 Alkylidenecyclopropane
K1 Cycloaddition
AB A Pd catalyst made from a Pd(0) source and a bulky biaryl phosphine ligand promotes highly efficient intramolecular (3 + 2) heterocycloadditions between alkylidenecyclopropanes (ACPs) and carbonyls. The annulations provide a straightforward access to fused polycyclic systems featuring β-methylene tetrahydrofuran moieties. DFT data support a pallada–ene process and shed light on the critical role of hemilabile interactions between the Pd center and the bulky biaryl phosphine. Significantly, these Pd(0) catalysts are also effective for promoting intermolecular formal cycloadditions between ACPs and trifluoromethyl ketones, thus providing for a direct entry to chiral tetrahydrofuran moieties (THFs) bearing trifluoromethyl–substituted carbons
PB American Chemical Society
YR 2020
FD 2020
LK http://hdl.handle.net/10347/23209
UL http://hdl.handle.net/10347/23209
LA eng
NO ACS Catal. 2020, 10, 14, 7710–7718
NO This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acscatal.0c01827
NO This work received financial support from the Spanish MINECO (SAF2016-76689-R, CTQ2017-84767-P), the Xunta de Galicia (ED431C 2017/19, 2015-CP082, Centro Singular de Investigación de Galicia accreditation 2019-2022, ED431G 2019/03, and a predoctoral Fellowship to E.d.C. and M.C.), CONICYT (grant to F.V.), and the ERDF, ERC (Adv. Grant 340055). The Orfeo–Cinqa network (CTQ2016-81797-REDC) is also acknowledged
DS Minerva
RD 28 abr 2026