Gold Catalyzed Decarboxylative Cross-Coupling of Iodoarenes

被引：36

作者：

Daley, Ryan A. ^{[1
]}

Morrenzin, Aaron S. ^{[2
]}

Neufeldt, Sharon R. ^{[2
]}

Topczewski, Joseph J. ^{[1
]}

机构：

[1] Univ Minnesota Twin Cities, Dept Chem, Minneapolis, MN 55455 USA

[2] Montana State Univ, Dept Chem & Biochem, Bozeman, MT 59717 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2020年 / 142卷 / 30期

基金：

美国国家科学基金会;

关键词：

VISIBLE-LIGHT PHOTOREDOX; OXIDATIVE ADDITION; LIGAND DESIGN; ARYL HALIDES; COMPLEXES; REACTIVITY; ACTIVATION; PALLADIUM; PROTODEBORONATION; ARENES;

D O I：

10.1021/jacs.0c06244

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 (F-ortho). 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.

引用

页码：13210 / 13218

页数：9

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