RT Journal Article
T1 Assembly of 2-substituted tetrahydroquinolines from ortho-methylbenzenesulfamides and dienes, using a C(sp3)-H activation/ annulation sequence
A1 Huertas.Morales, Iván
A1 Cendón, Borja
A1 Costa, Domingo
A1 Gulías Costa, Moisés
AB 1,2,3,4-Tetrahydroquinolines (THQs) are essential structural cores in many natural products and pharmaceutical drugs. Especially relevant are those presenting substitutions at position 2, yet practical methods for their one-step assembly from acyclic precursors are very scarce. Herein, we present a straightforward approach to assembling these skeletons from ortho-methylanilines using a palladium-catalyzed C(sp3)–H activation/formal cycloaddition sequence. Key for the success of the approach is the use of dienes as partners, since they lead to stable π–allyl palladium intermediates that prevent β-hydride elimination processes and allow installation of versatile alkenyl handles at position 2. Moreover, installing a perfluorobenzenesulfonyl substituent at the amine not only facilitates the C–H activation but also allows for an easy recovery of the free amine.
PB ACS
YR 2024
FD 2024
LK https://hdl.handle.net/10347/37554
UL https://hdl.handle.net/10347/37554
LA eng
NO Huertas-Morales, I.; Cendón, B.; Costa, D.; Mascareñas, J. L.; Gulías, M. (2024), Assembly of 2-substituted tetrahydroquinolines from ortho-methylbenzenesulfamides and dienes, using a C(sp3)-H activation/ annulation sequence. Org. Lett., 26: 7789–7794. doi: 10.1021/acs.orglett.4c02292
NO This is the peer reviewed version of the following article: Huertas-Morales, I.; Cendón, B.; Costa, D.; Mascareñas, J. L.; Gulías, M. (2024), Assembly of 2-substituted tetrahydroquinolines from ortho-methylbenzenesulfamides and dienes, using a C(sp3)-H activation/ annulation sequence. Org. Lett., 26: 7789–7794, which has been published in final form at https://doi.org/10.1021/acs.orglett.4c02292. This article may be used for non-commercial purposes in accordance with ACS Terms and Conditions for Use of SelfArchived Versions.
NO This work has received financial support from Spanish grants (Grants PID2022-137318OB-I00 and PID2022-136785NB-I00 funded by MCIN/AEI/10.13039/501100011033, Grant IHRC22-00009 funded by MCIN/ISCIII and by the “European Union NextGenerationEU/PRTR”, and ORFEO-CINQA network RED2022-134287-T), 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 corresponding to the multiannual financial framework 2014-2020). We thank the Ministerio de Universidades for the FPU fellowship to I.H.
DS Minerva
RD 29 abr 2026