Kumada Arylation of Secondary Amides Enabled by Chromium Catalysis for Unsymmetric Ketone Synthesis under Mild Conditions

被引：55

作者：

Chen, Changpeng ^{[1
,2
]}

Liu, Pei ^{[1
]}

Luo, Meiming ^{[2
]}

Zeng, Xiaoming ^{[1
,2
]}

机构：

[1] Xi An Jiao Tong Univ, Frontier Inst Sci & Technol, Xian 710054, Shaanxi, Peoples R China

[2] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

ACS CATALYSIS | 2018年 / 8卷 / 07期

基金：

中国国家自然科学基金;

关键词：

chromium; homogeneous catalysis; Kumada reaction; amides; ketones; CROSS-COUPLING REACTIONS; ROOM-TEMPERATURE; GRIGNARD-REAGENTS; GENERAL-METHOD; BOND-CLEAVAGE; NICKEL; ARYL; ACTIVATION; ETHERS; ARYLMAGNESIATION;

D O I：

10.1021/acscatal.8b01380

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The synthesis of aromatic ketones by chromium-catalyzed Kumada arylation of secondary amides with organomagnesium reagents is described. This reaction was enabled by using low-cost chromium(III) salt as a precatalyst, combined with trimethylsilyl chloride as an additive, and presents a rare example of catalytic transformation of secondary amides to ketones at room temperature. It was shown that catalytically active low-valent chromium species might be responsible for the amide ketone exchange by mechanism involving the activation of benzimidate intermediate.

引用

页码：5864 / +

页数：9

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