Gold Catalyzed Decarboxylative Cross-Coupling of Iodoarenes

Ryan A. Daley, Aaron S. Morrenzin, Sharon R. Neufeldt, Joseph J. Topczewski

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

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). 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). Reactions with isolated gold complexes and DFT calculations support a mechanism proceeding through oxidative addition at a gold(I) cation with decarboxylation being viable at either a gold(I) or a silver(I) species.

Original languageEnglish (US)
Pages (from-to)13210-13218
Number of pages9
JournalJournal of the American Chemical Society
Volume142
Issue number30
DOIs
StatePublished - Jul 29 2020

Bibliographical note

Funding Information:
Jenna Humke, Brendan Graziano, and Dr. Victor Young are gratefully acknowledged for assistance collecting the crystal structure of complex Ag1 . This work was supported by the University of Minnesota. Financial support was provided by the National Science Foundation Award No. CHE1942223 (J.J.T. and R.A.D.). A.S.M. and S.R.N. are grateful to Montana State University for support. Calculations were performed on Comet at SDSC and Bridges at the Pittsburgh Supercomputing Center through XSEDE (CHE190050), which is supported by NSF (ACI-1548562), as well as on the Hyalite High Performance Computing System at MSU.

Publisher Copyright:
Copyright © 2020 American Chemical Society.

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