RT Journal Article
T1 Mechanistic Studies on the Synthesis of Pyrrolidines and Piperidines via Copper-Catalyzed Intramolecular C–H Amination
A1 Muñoz Molina, José María
A1 Bafaluy, Daniel
A1 Funes Ardoiz, Ignacio
A1 Aguirre, Adiran J. de
A1 Maseras, Feliu
A1 Rodríguez Belderraín, Tomás
A1 Pérez Romero, Pedro José
A1 Muñiz, Kilian
AB We have recently developed a method for the synthesis of pyrrolidines and piperidines via intramolecular C–H amination of N-fluoride amides using [TpxCuL] complexes as precatalysts [Tpx = tris(pyrazolyl)borate ligand and L = THF or CH3CN]. Herein, we report mechanistic studies on this transformation, which includes the isolation and structural characterization of a fluorinated copper(II) complex, [(TpiPr2OH)CuF] [TpiPr = hydrotris(3,5-diisopropylpyrazolyl)borate], pertinent to the mechanistic pathway. The effects of the nature of the Tpx ligand in the copper catalyst as well as of the halide in the N–X amides employed as reactants have been investigated both from experimental and computational perspectives.
PB American Chemical Society
SN 0276-7333
SN 1520-6041 (electrónico)
YR 2022
FD 2022
LK http://hdl.handle.net/10272/21255
UL http://hdl.handle.net/10272/21255
LA eng
NO Muñoz-Molina, J. M., Bafaluy, D., Funes-Ardoiz, I., de Aguirre, A., Maseras, F., Belderrain, T. R., Pérez, P. J., & Muñiz, K. (2022). Mechanistic Studies on the Synthesis of Pyrrolidines and Piperidines via Copper-Catalyzed Intramolecular C–H Amination. In Organometallics (Vol. 41, Issue 9, pp. 1099–1105). American Chemical Society (ACS). https://doi.org/10.1021/acs.organomet.2c00095
NO We thank the Ministerio de Ciencia e Innovación (PID2020-113797RB-C21, PID2020-112825RB-I00, CTQ2017-88496-R,and CEX2019-000925-S), COST Action CA15106 “C−HActivation in Organic Synthesis (CHAOS)”and Red Intecat(CTQ2016-81923-REDC), and Universidad de Huelva(P.O.Feder 2014-2020 UHU-1254043). We thank Universidadde Huelva/CBUA for funding for open access charge.
DS Repositorio Institucional de la Universidad de Huelva
RD 30 may 2026