RT Journal Article
T1 Copper-Catalyzed N-F Bond Activation for Uniform Intramolecular C-H Amination Yielding Pyrrolidines and Piperidines
A1 Bafaluy, Daniel
A1 Muñoz Molina, José María
A1 Funes Ardoiz, Ignacio
A1 Herold, Sebastian
A1 Aguirre, Adiran J. de
A1 Zhang, Hongwei
A1 Maseras, Feliu
A1 Rodríguez Belderraín, Tomás
A1 Pérez Romero, Pedro José
A1 Muñiz, Kilian
AB The dual function of the N-F bond as an effective oxidant and subsequent nitrogen source in intramolecular aliphatic C-H functionalization reactions is explored. Copper catalysis is demonstrated to exercise full regio- and chemoselectivity control, which opens new synthetic avenues to nitrogenated heterocycles with predictable ring sizes. For the first time, a uniform catalysis manifold has been identified for the construction of both pyrrolidine and piperidine cores. The individual steps of this new copper oxidation catalysis were elucidated by control experiments and computational studies, clarifying the singularity of the N-F function and characterizing the catalytic cycle to be based on a copper(I/II) manifold.
PB Wiley
SN 1433-7851
SN 1521-3773 (electrónico)
YR 2019
FD 2019-06
LK http://hdl.handle.net/10272/19636
UL http://hdl.handle.net/10272/19636
LA eng
NO Bafaluy D, Muñoz-Molina JM, Funes-Ardoiz I, Herold S, de Aguirre AJ, Zhang H, Maseras F, Belderrain TR, Pérez PJ, Muñiz K. Activación de bonos N-F catalizados de cobre para Aminación intramolecular uniforme C-H que produce pirrolidinas y piperidinas. Angew Chem Int Ed Engl. 2019 Junio 24;58(26):8912-8916. doi: 10.1002/anie.201902716. Epub 2019 20 de mayo. PMID: 30997949.
NO We thank MINECO for Grants CTQ2017-82893-C2-1-R, CTQ2017-87792-R, CTQ2017-88496-R, COST Action CA15106 “C–H Activation in Organic Synthesis (CHAOS)”and Red Intecat (CTQ2016-81923-REDC).
DS Repositorio Institucional de la Universidad de Huelva
RD 1 jun 2026