Copper-Catalyzed N−F Bond Activation for Uniform Intramolecular C−H Amination Yielding Pyrrolidines and Piperidines

Daniel Bafaluy, José María Muñoz-Molina, Ignacio Funes-Ardoiz, Sebastian Herold, Adiran J. de Aguirre, Hongwei Zhang, Feliu Maseras, Tomás R. Belderrain, Pedro J. Pérez, Kilian Muñiz

Research output: Contribution to journalArticleResearch

16 Citations (Scopus)

Abstract

© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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.
Original languageEnglish
Pages (from-to)8912-8916
JournalAngewandte Chemie - International Edition
Volume58
DOIs
Publication statusPublished - 24 Jun 2019

Keywords

  • amination
  • copper catalysis
  • C−H bond activation
  • C−N bond formation
  • DFT calculations

Fingerprint Dive into the research topics of 'Copper-Catalyzed N−F Bond Activation for Uniform Intramolecular C−H Amination Yielding Pyrrolidines and Piperidines'. Together they form a unique fingerprint.

  • Cite this

    Bafaluy, D., Muñoz-Molina, J. M., Funes-Ardoiz, I., Herold, S., de Aguirre, A. J., Zhang, H., Maseras, F., Belderrain, T. R., Pérez, P. J., & Muñiz, K. (2019). Copper-Catalyzed N−F Bond Activation for Uniform Intramolecular C−H Amination Yielding Pyrrolidines and Piperidines. Angewandte Chemie - International Edition, 58, 8912-8916. https://doi.org/10.1002/anie.201902716