Metal-Catalyzed Dealkoxylative Caryl-Csp3 Cross-Coupling-Replacement of Aromatic Methoxy Groups of Aryl Ethers by Employing a Functionalized Nucleophile

被引：111

作者：

Leiendecker, Matthias ^{[1
]}

Hsiao, Chien-Chi ^{[1
]}

Guo, Lin ^{[1
]}

Alandini, Nurtalya ^{[1
]}

Rueping, Magnus ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 47期

关键词：

aryl ethers; C-O bond cleavage; cross-coupling; methoxy functionalization; nickel; C-O BONDS; DIRECTED ORTHO-METALATION; CARBON-CARBON BONDS; GRIGNARD-REAGENTS; POLYSUBSTITUTED AROMATICS; ORGANOALUMINUM REAGENTS; SUBSTITUTED ANISOLES; ORGANIC-SYNTHESIS; ION REACTIONS; ENOL ETHERS;

D O I：

10.1002/anie.201402922

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The direct replacement of aromatic methoxy groups with activated carbon nucleophiles would give rise to novel synthetic pathways for targeted and diversity-oriented syntheses. We demonstrate here that this transformation can be achieved in a one-step reaction involving a bifunctional organolithium nucleophile in combination with a C-Ar-OMe bond-cleaving nickel catalyst. The resulting products are stable, alpha-CH active, and suitable for various further modifications.

引用

页码：12912 / 12915

页数：4