Gold Catalyzed Decarboxylative Cross-Coupling of Iodoarenes

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

doi:10.1021/jacs.0c06244

Gold Catalyzed Decarboxylative Cross-Coupling of Iodoarenes

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

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

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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 language	English (US)
Pages (from-to)	13210-13218
Number of pages	9
Journal	Journal of the American Chemical Society
Volume	142
Issue number	30
DOIs	https://doi.org/10.1021/jacs.0c06244
State	Published - Jul 29 2020

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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.",

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AB - 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.

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Gold Catalyzed Decarboxylative Cross-Coupling of Iodoarenes

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