A Further Decrease in the Catalyst Loading for the Palladium-Catalyzed Direct Intramolecular Arylation of Amides and Sulfonamides

被引：30

作者：

Conde, Nerea ^{[1
]}

Churruca, Fatima ^{[1
]}

SanMartin, Raul ^{[1
]}

Teresa Herrero, Maria ^{[1
]}

Dominguez, Esther ^{[1
]}

机构：

[1] Univ Basque Country UPV EHU, Fac Sci & Technol, Dept Organ Chem 2, Leioa 48940, Spain

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 07期

关键词：

biaryl sultams; C-H arylation; palladium; phenanthridinones; pincer complexes; HETEROGENEOUS CATALYSIS; HOMOGENEOUS CATALYSTS; PINCER COMPLEXES; ARYL BROMIDES; SUZUKI; HECK; CHEMISTRY; EFFICIENT; COUPLINGS; PATHWAY;

D O I：

10.1002/adsc.201401129

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The direct arylation of N-substituted o-bromobenzanilides and benzenesulfonamides via C-H bond functionalization has been developed using very low catalyst loadings. This novel cost-effective and more sustainable method relies on a PCN-type palladium pincer complex as a highly active palladium source, providing a general and efficient access to phenanthridinones, biaryl sultams and related heterocyclic systems. The beneficial effect of water as cosolvent has been observed in this process, which is not seriously influenced by electronic effects at the arene moieties or sterically demanding substituents at the amide or sulfonamide nitrogen. In addition, a number of experiments (kinetic plot, poisoning assays, TEM, ESI) have been performed in order to understand the role of the employed palladium complex in this reaction.

引用

页码：1525 / 1531

页数：7

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