A Mild, Ferrocene-Catalyzed C-H Imidation of (Hetero)Arenes

被引：189

作者：

Foo, Klement ^{[1
]}

Sella, Eran ^{[1
]}

Thome, Isabelle ^{[1
]}

Eastgate, Martin D. ^{[2
]}

Baran, Phil S. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Bristol Myers Squibb, Chem Dev, New Brunswick, NJ 08903 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 14期

关键词：

N BOND FORMATION; OXIDATIVE FUNCTIONALIZATION; DIRECT AMINATION; AMIDATION; SUBSTITUTION; RADICALS; NITROGEN; ARENES; ROUTE; DECARBOXYLATION;

D O I：

10.1021/ja501879c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple method for direct C-H imidation is reported using a new perester-based self-immolating reagent and a base-metal catalyst. The succinimide products obtained can be easily deprotected in situ (if desired) to reveal the corresponding anilines directly. The scope of the reaction is broad, the conditions are extremely mild, and the reaction is tolerant of oxidizable and acidlabile functionality, multiple heteroatoms, and aryl iodides. Mechanistic studies indicate that ferrocene (Cp2Fe) plays the role of an electron shuttle in the decomposition of the perester reagent, delivering a succinimidyl radical ready to add to an aromatic system.

引用

收藏

页码：5279 / 5282

页数：4

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