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Gold Catalyzed Decarboxylative Cross-Coupling of Iodoarenes

preprint
submitted on 12.03.2020 and posted on 13.03.2020 by Ryan A. Daley, Joseph Topczewski
This report details a decarboxylative cross-coupling of (hetero)aryl carboxylates with iodoarenes in the presence of a gold catalyst (>25 examples, up to 96% yield). Generating an aryl nucleophile via decarboxylation obviates problems associated with transmetalation at a putative gold(III) complex. This reaction is site specific, which overcomes prior limitations associated with gold catalyzed oxidative coupling reactions. The reactivity of the (hetero)aryl carboxylate correlates qualitatively to the field effect parameter (Fortho). Furthermore, each step in a proposed mechanism was observed from isolated gold complexes, supporting a gold catalyzed mechanism.

Funding

University of Minnesota

History

Email Address of Submitting Author

jtopczew@umn.edu

Institution

University of Minnesota

Country

United States

ORCID For Submitting Author

0000-0002-9921-5102

Declaration of Conflict of Interest

None

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in Journal of the American Chemical Society

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