Palladium(II)-Catalyzed Regioselective Arylation of Naphthylamides with Aryl Iodides Utilizing a Quinolinamide Bidentate System

被引：79

作者：

Huang, Lehao ^{[1
]}

Li, Qian ^{[1
,2
]}

Wang, Chen ^{[1
]}

Qi, Chenze ^{[1
]}

机构：

[1] Shaoxing Univ, Inst Appl Chem, Zhejiang Key Lab Alternat Technol Fine Chem Proc, Shaoxing 312000, Zhejiang, Peoples R China

[2] Ningbo Univ, Coll Mat Sci & Chem Engn, Ningbo 310014, Zhejiang, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 07期

关键词：

CATALYZED DIRECT ARYLATION; C-H ARYLATION; UNACTIVATED C(SP(3))-H; BOND-FORMATION; SIMPLE ARENES; AROMATIC AMIDES; ACTIVATION; RUTHENIUM; FUNCTIONALIZATION; (HETERO)ARENES;

D O I：

10.1021/jo400017v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium(II)-catalyzed quinolinamide-directed 8-arylation of 1-naphthylamides with aryl iodides is reported. The bidentate directing group (quinolinamide) proved to be crucial for a highly regioselective transformation. In addition, the amide directing group can be easily hydrolyzed under basic conditions to offer a range of 8-aryl-1-naphthylamine derivatives. The theoretical calculations suggest that the C-H arylation reaction proceeds through a sequential C-H activation/oxidative addition pathway.

引用

页码：3030 / 3038

页数：9

共 83 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] 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

[3] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[4] Role of Explicit Solvents in Palladium(II)-Catalyzed Alkoxylation of Arenes: An Interesting Paradigm for Preferred Outer-Sphere Reductive Elimination over Inner-Sphere Pathway [J].

Anand, Megha ;

Sunoj, Raghavan B. .

ORGANOMETALLICS, 2012, 31 (17) :6466-6481

[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] Mechanistic and Computational Studies of Oxidatively-Induced Aryl-CF3 Bond-Formation at Pd: Rational Design of Room Temperature Aryl Trifluoromethylation [J].

Ball, Nicholas D. ;

Gary, J. Brannon ;

Ye, Yingda ;

Sanford, Melanie S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (19) :7577-7584

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

Baudoin, Olivier .

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

[8] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[9] Twofold C-H functionalization:: Palladium-catalyzed ortho arylation of anilides [J].

Brasche, Gordon ;

Garcia-Fortanet, Jorge ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2008, 10 (11) :2207-2210

[10] DEVELOPMENT OF ORGANOPALLADIUM(IV) CHEMISTRY - FUNDAMENTAL-ASPECTS AND SYSTEMS FOR STUDIES OF MECHANISM IN ORGANOMETALLIC CHEMISTRY AND CATALYSIS [J].

CANTY, AJ .

ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (02) :83-90

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