Rhodium-Catalyzed Alkylation of C-H Bonds in Aromatic Amides with α,β-Unsaturated Esters

被引：83

作者：

Shibata, Kaname ^{[1
]}

Chatani, Naoto ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 19期

基金：

日本科学技术振兴机构;

关键词：

BIDENTATE-CHELATION ASSISTANCE; UNACTIVATED C(SP(3))-H BONDS; CARBOXYLIC-ACID DERIVATIVES; CONJUGATE ADDITION; ALIPHATIC AMIDES; DIRECT ARYLATION; MILD CONDITIONS; DIRECTING GROUP; RUTHENIUM; ACTIVATION;

D O I：

10.1021/ol502500c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The alkylation of C-H bonds with alpha,beta-unsaturated carbonyl compounds by a rhodium catalyzed reaction of aromtic amides containing an 8-aminoquinoline moiety is reported. The reaction is highly regioselective. The formation of C-C bonds occurs between the ortho C-H bonds in aromatic amides and the beta-position of the acyclic alpha,beta-unsaturated carbonyl compounds. The reaction is applicable to various acyclic-alpha,beta-unsaturated carbonyl compounds, such as acrylic esters, fumarate, meleate, and phenyl vinyl sulfone.

引用

页码：5148 / 5151

页数：4

共 56 条

[1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].

Ackermann, Lutz .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295

[2] Ruthenium-Catalyzed Oxidative C-H Alkenylations of Anilides and Benzamides in Water [J].

Ackermann, Lutz ;

Wang, Lianhui ;

Wolfram, Ratnakancana ;

Lygin, Alexander V. .

ORGANIC LETTERS, 2012, 14 (03) :728-731

[3] Metal-catalyzed direct alkylations of (hetero)arenes via C-H bond cleavages with unactivated alkyl halides [J].

Ackermann, Lutz .

CHEMICAL COMMUNICATIONS, 2010, 46 (27) :4866-4877

[4] Nickel-Catalyzed Direct Arylation of C(sp3)-H Bonds in Aliphatic Amides via Bidentate-Chelation Assistance [J].

Aihara, Yoshinori ;

Chatani, Naoto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (03) :898-901

[5] Nickel-Catalyzed Direct Alkylation of C-H Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance [J].

Aihara, Yoshinori ;

Chatani, Naoto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5308-5311

[6] Ruthenium-catalyzed direct arylation of C-H bonds in aromatic amides containing a bidentate directing group: significant electronic effects on arylation [J].

Aihara, Yoshinori ;

Chatani, Naoto .

CHEMICAL SCIENCE, 2013, 4 (02) :664-670

[7] Diastereoselective Carbocyclization of 1,6-Heptadienes Triggered by Rhodium-Catalyzed Activation of an Olefinic C-H Bond [J].

Aissa, Christophe ;

Ho, Kelvin Y. T. ;

Tetlow, Daniel J. ;

Pin-No, Maria .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (16) :4209-4212

[8] Palladium-Catalyzed Direct ortho-Alkynylation of Aromatic Carboxylic Acid Derivatives [J].

Ano, Yusuke ;

Tobisu, Mamoru ;

Chatani, Naoto .

ORGANIC LETTERS, 2012, 14 (01) :354-357

[9] Palladium-Catalyzed Direct Ethynylation of C(sp3)-H Bonds in Aliphatic Carboxylic Acid Derivatives [J].

Ano, Yusuke ;

Tobisu, Mamoru ;

Chatani, Naoto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) :12984-12986

[10]

[Anonymous], 2012, U.S. Pat. Appl. Publ., Patent No. 20120270915

← 1 2 3 4 5 6 →