Copper-Catalyzed Intramolecular Benzylic C-H Amination for the Synthesis of Isoindolinones

被引：70

作者：

Yamamoto, Chiaki ^{[1
]}

Takamatsu, Kazutaka ^{[1
]}

Hirano, Koji ^{[1
]}

Miura, Masahiro ^{[1
]}

机构：

[1] Osaka Univ, Dept Appl Chem, Grad Sch Engn, Suita, Osaka 5650871, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 17期

关键词：

INTERMOLECULAR DIRECT ARYLATION; N BOND FORMATION; C(SP(3))-H; PALLADIUM; ACTIVATION; MECHANISM; FUNCTIONALIZATION; DERIVATIVES; CYCLIZATION; AMIDATION;

D O I：

10.1021/acs.joc.6b01393

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed intramolecular amination occurs at the benzylic C-H of 2-methylbenzamides to deliver the corresponding isoindolinones of great interest in medicinal chemistry. The mild and abundant MnO2 works well as a terminal oxidant, and the reaction proceeds smoothly under potentially explosive organic peroxide-free conditions. Additionally, the directing-group-dependent divergent mechanisms are proposed: 8-aminoquinoline-containing benzamides include a Cu-mediated organometallic pathway whereas an aminyl radical-promoted Hofmann-Loffler-Freytag (HLF)-type mechanism can be operative in the case of N-naphthyl-substituted substrates.

引用

页码：7675 / 7684

页数：10

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