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Aminopotassiation by mixed potassium/lithium amides: a synthetic path to difficult to access phenethylamine derivates

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journal contribution
posted on 19.11.2021, 15:05 by Andreas Seymen, Ulrike Opper, Andreas Voß, Lukas Brieger, Felix Otte, Christian Unkelbach, Donal O'SheaDonal O'Shea, Carsten Strohmann
Insights gained from a comparison of aminometalation reactions with lithium amides, potassium amides and mixed lithium/potassium amides are presented. A combination of structural characterization, DFT calculations and electrophile reactions of aminometalated intermediates has shown the advantages of using a mixed metal strategy. While potassium amides fail to add, the lithium amides are uncontrollable and eliminated, yet the mixed K/Li amides deliver the best of both systems. Aminopotassiation proceeds to form the alkylpotassium species which has enhanced stability over its lithium counterpart allowing for its isolation and thereby its further characterization.

Funding

Deutsche Forschungsgemeinschaft (DFG)

Studienstiftung des deutschen Volkes

Fonds der Chemischen Industrie (FCI)

Bischöfliche Studienförderung Cusanuswerk

Projekt DEAL

History

Comments

The original article is available at https://onlinelibrary.wiley.com German version: https://doi.org/10.1002/ange.202009318 and https://hdl.handle.net/10779/rcsi.16998742.v1

Published Citation

Seymen A. et al. Aminopotassiation by mixed potassium/lithium amides: a synthetic path to difficult to access phenethylamine derivates. Angew Chem Int Ed Engl. 2020;59(50):22500-22504.

Publication Date

26 August 2020

PubMed ID

32846026

Department/Unit

  • Chemistry

Research Area

  • Cancer
  • Surgical Science and Practice
  • Chemistry and Pharmaceutical Sciences

Publisher

Wiley

Version

  • Published Version (Version of Record)