ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
Cat_Guideline_Amine_Suzuki_Pd.pdf (1.54 MB)

Curse or Blessing? Influence of Impurities on Cross-Coupling— Guideline for Elucidating Catalysts

preprint
submitted on 21.02.2021, 16:21 and posted on 23.02.2021, 11:54 by Zoltán Novák, Réka Adamik, János T. Csenki, Ferenc Béke, Regina Gavaldik, Bálint Varga, Bálint Nagy, Zoltán May, János Daru, Zsombor Gonda, Gergely L. Tolnai
Several efforts have been made for the replacement of noble metal palladium in cross-coupling reactions, maintaining high efficiency of the target transformation. In several cases it is possible to perform the chemistry of palladium with related metals, and their activity was supported with mechanistic studies. Moreover, the complete exclusion of palladium is also in focus. Very recently it was demonstrated that special amine organocatalysts could catalyse Suzuki-Miyaura coupling reaction. Here we show that in this recent transformation homeopathic palladium impurities and trace phosphorous species originated from the conditions used for the organocatalyst synthesis are responsible for the catalytic effect instead of the amine species. This finding confirms the power of palladium in cross-coupling and draw the attention of impurity effect in this field of chemical research. In this article, we represent general guidelines for elucidating the real catalyst of reactions.

Funding

No. K132077, K124592, K130048

Bolyai/536/20 and ÚNKP-20-5.

NKFIH-1157-8/2019-DT

History

Email Address of Submitting Author

tolnai@chem.elte.hu

Institution

Eötvös University

Country

Hungary

ORCID For Submitting Author

0000-0002-5253-5117

Declaration of Conflict of Interest

No conflict of interest.

Exports

ChemRxiv

Exports