Pd(II)-Catalyzed Intermolecular Arylation of Unactivated C(sp3)-H Bonds with Aryl Bromides Enabled by 8-Aminoquinoline Auxiliary

被引：82

作者：

Wei, Yu ^{[1
,2
]}

Tang, Huarong ^{[3
]}

Cong, Xuefeng ^{[1
,2
]}

Rao, Bin ^{[1
,2
]}

Wu, Chao ^{[1
,2
]}

Zeng, Xiaoming ^{[1
,2
]}

机构：

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

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

[3] Xi An Jiao Tong Univ, Sch Mat Sci & Engn, Xian 710054, Shaanxi, Peoples R China

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 08期

基金：

中国国家自然科学基金;

关键词：

C-H BONDS; CATALYZED DIRECT ARYLATION; INTRAMOLECULAR ALKANE ARYLATION; DIRECTING GROUP; STEREOSELECTIVE-SYNTHESIS; AROMATIC CARBOXAMIDES; COUPLING REACTIONS; C(SP(2))-H BONDS; PALLADIUM; FUNCTIONALIZATION;

D O I：

10.1021/ol500745t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

: An example of using readily available, less reactive aryl bromides as arylating reagents in the Pd(II)-catalyzed intermolecular arylation of unactivated C(sp(3))-H bonds is described. This reaction was promoted by a crucial 8-aminoquinolinyl directing group and a K2CO3 base, enabling regiospecific installation of an aryl scaffold at the beta-position of carboxamides. A mechanistic study by DFT calculations reveals a C(sp(3))-H activation-led pathway featuring the oxidative addition as the highest energy transition state.

引用

页码：2248 / 2251

页数：4

共 57 条

[1] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Kapdi, Anant R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826

[2] 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

[3] 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

[4] 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

[5] 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

[6]

[Anonymous], MODERN ARYLATION MET

[7]

[Anonymous], 2012, CATALYSIS METAL COMP

[8] Iron-Catalyzed Ortho-Allylation of Aromatic Carboxamides with Allyl Ethers [J].

Asako, Sobi ;

Ilies, Laurean ;

Nakamura, Eiichi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (47) :17755-17757

[9] Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds [J].

Baudoin, Olivier .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4902-4911

[10] Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides [J].

Bellina, Fabio ;

Rossi, Renzo .

CHEMICAL REVIEWS, 2010, 110 (02) :1082-1146

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