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These are preliminary reports that have not been peer-reviewed.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

A Widely Applicable Dual-Catalytic System for Cross-Electrophile Coupling

preprint
submitted on 26.06.2020 and posted on 29.06.2020 by David Charboneau, Emily L. Barth, Nilay Hazari, Mycah R. Uehling, Susan L. Zultanski
A new dual catalytic system for cross-electrophile coupling reactions between aryl and alkyl halides that features a Ni catalyst, a Co co-catalyst, and a mild homogeneous reductant, is described. This is a unique combination of reagents for cross-electrophile coupling reactions, which results in one of the most versatile systems reported to date. For example, the coupling of aryl bromides and aryl iodides with alkyl bromides, alkyl iodides, alkyl mesylates, and benzyl chlorides is demonstrated under similar reaction conditions. The system is tolerant of numerous functional groups and is capable of coupling heteroaryl halides, di-ortho-substituted aryl halides, pharmaceutically relevant drug-like aryl halides, and a diverse range of alkyl halides. Additionally, the dual catalytic platform facilitates a series of novel one-pot three-component cross-electrophile coupling reactions of bromo(iodo)arenes with two distinct alkyl halides. Mechanistic studies indicate that the Ni catalyst activates the aryl halide electrophile, while the Co catalyst activates the alkyl electrophile.

History

Email Address of Submitting Author

david.charboneau@yale.edu

Institution

Yale University

Country

United States of America

ORCID For Submitting Author

0000-0003-4181-9269

Declaration of Conflict of Interest

The authors declare no competing financial interest.

Licence

Exports

Logo branding

Licence

Exports