Chromium-Catalyzed Activation of Acyl C-O Bonds with Magnesium for Amidation of Esters with Nitroarenes

被引：54

作者：

Ling, Liang ^{[1
]}

Chen, Changpeng ^{[1
,2
]}

Luo, Meiming ^{[1
]}

Zeng, Xiaoming ^{[1
,2
]}

机构：

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

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

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 06期

基金：

中国国家自然科学基金;

关键词：

SECONDARY AMIDES; GRIGNARD-REAGENTS; TRANSAMIDATION; CLEAVAGE; ETHERS; ARYLMAGNESIATION; REDUCTION; COMPLEX; ACIDS;

D O I：

10.1021/acs.orglett.9b00554

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Here, we report a chromium-catalyzed activation of acyl C-O bonds with magnesium for amidation of esters with nitroarenes. Low-cost chromium(III) chloride shows high reactivity in promoting amidation by using magnesium as reductant and chlorotrimethylsilane as additive. It provides a step-economic strategy to the synthesis of centrally important amide motifs using inexpensive and air-stable nitroarenes as amino sources.

引用

页码：1912 / 1916

页数：5

共 49 条

[11] Nickel-Catalyzed Reductive Transamidation of Secondary Amides with Nitroarenes [J].

Cheung, Chi Wai ;

Ploeger, Marten Leendert ;

Hu, Xile .

ACS CATALYSIS, 2017, 7 (10) :7092-7096

[12] Direct amidation of esters with nitroarenes [J].

Cheung, Chi Wai ;

Ploeger, Marten Leendert ;

Hu, Xile .

NATURE COMMUNICATIONS, 2017, 8

[13] Low-Valent, High-Spin Chromium-Catalyzed Cleavage of Aromatic Carbon Nitrogen Bonds at Room Temperature: A Combined Experimental and Theoretical Study [J].

Cong, Xuefeng ;

Fan, Fei ;

Ma, Pengchen ;

Luo, Meiming ;

Chen, Hui ;

Zeng, Xiaoming .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (42) :15182-15190

[14] Regio- and Chemoselective Kumada Tamao Corriu Reaction of Aryl Alkyl Ethers Catalyzed by Chromium Under Mild Conditions [J].

Cong, Xuefeng ;

Tang, Huarong ;

Zeng, Xiaoming .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (45) :14367-14372

[15] Metal-catalyzed activation of ethers via C-O bond cleavage: a new strategy for molecular diversity [J].

Cornella, Josep ;

Zarate, Cayetana ;

Martin, Ruben .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (23) :8081-8097

[16] Nickel-catalyzed transamidation of aliphatic amide derivatives [J].

Dander, Jacob E. ;

Baker, Emma L. ;

Garg, Neil K. .

CHEMICAL SCIENCE, 2017, 8 (09) :6433-6438

[17] Nonclassical Routes for Amide Bond Formation [J].

de Figueiredo, Renata Marcia ;

Suppo, Jean-Simon ;

Campagne, Jean-Marc .

CHEMICAL REVIEWS, 2016, 116 (19) :12029-12122

[18]

Docherty JH, 2017, NAT CHEM, V9, P595, DOI [10.1038/nchem.2697, 10.1038/NCHEM.2697]

[19] Carbon-carbon bond formations involving organochromium(III) reagents [J].

Fürstner, A .

CHEMICAL REVIEWS, 1999, 99 (04) :991-1045

[20] Synthesis of Amides from Esters and Amines with Liberation of H2 under Neutral Conditions [J].

Gnanaprakasam, Boopathy ;

Milstein, David .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (06) :1682-1685

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