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These are preliminary reports that have not been peer-reviewed.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.
1/1
0/0

Dual Nickel/Palladium-Catalyzed Reductive Cross-Coupling Reactions Between Two Phenol Derivatives

preprint
submitted on 08.06.2020 and posted on 11.06.2020 by Baojian Xiong, Yue Li, Yin Wei, Søren Kramer, Zhong Lian
Cross-coupling between substrates that can be easily derived from phenols is highly attractive due to the abundance and low cost of phenols. Here, we report a dual nickel/palladium-catalyzed reductive cross-coupling between aryl tosylates and aryl triflates; both substrates can be accessed in just one step from readily available phenols. The reaction has a broad functional group tolerance and substrate scope (>60 examples). Furthermore, it displays low sensitivity to steric effects demonstrated by the synthesis of a 2,2’disubstituted biaryl and a fully substituted aryl product. The widespread presence of phenols in natural products and pharmaceuticals allow for straightforward late-stage functionalization, illustrated with examples such as Ezetimibe and tyrosine. NMR spectroscopy and DFT calculations indicate that the nickel catalyst is responsible for activating the aryl triflate, while the palladium catalyst preferentially reacts with the aryl tosylate.

Funding

This work is supported by National Natural Science Foundation (21901168), ‘1000-Youth Talents Plan’, and Sichuan University (Z.L.). S.K. thanks the Lundbeck Foundation (R250-2017-1292) and the Technical University of Denmark for generous financial support. Y.W. thanks National Science Foundation (21772226) for financial support.

History

Email Address of Submitting Author

sokr@kemi.dtu.dk

Institution

Technical University of Denmark

Country

Denmark

ORCID For Submitting Author

0000-0001-6075-9615

Declaration of Conflict of Interest

The authors declare no competing interests.

Exports