Transition metal-catalyzed decarboxylative coupling reactions of alkynyl carboxylic acids

被引：192

作者：

Park, Kyungho ^{[1
]}

Lee, Sunwoo ^{[1
]}

机构：

[1] Chonnam Natl Univ, Dept Chem, Kwangju 500757, South Korea

来源：

RSC ADVANCES | 2013年 / 3卷 / 34期

基金：

新加坡国家研究基金会;

关键词：

PROPIOLIC ACID; ARYL HALIDES; C-C; DIARYLALKYNES; ACTIVATION; ALDEHYDES; IODIDES; CARBON;

D O I：

10.1039/c3ra41442f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The decarboxylative coupling of alkynyl carboxylic acids is an attractive area of research in organic chemistry, because the structure of aryl alkyne is one of the important building blocks for the synthesis of p-conjugated compounds. The use of alkynyl carboxylic acid as an alkyne source has several advantages in handling and storage. As a catalyst, palladium, copper, nickel, and silver were employed in the decarboxylative coupling reactions. The formation of C-C (sp(2)-sp, sp-sp and sp(3)-sp), C-N, C-P and C-S bonds has been developed. This review aims to illustrate the development of the decarboxylative coupling reaction of alkynyl carboxylic acids.

引用

页码：14165 / 14182

页数：18

共 68 条

[11] Catalytic C-H Bond Stannylation: A New Regioselective Pathway to C-Sn Bonds via C-H Bond Functionalization [J].

Doster, Meghan E. ;

Hatnean, Jillian A. ;

Jeftic, Tamara ;

Modi, Sunjay ;

Johnson, Samuel A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (34) :11923-11925

[12] Palladium-catalyzed decarboxylative cross-coupling of alkynyl carboxylic acids with arylboronic acids [J].

Feng, Chao ;

Loh, Teck-Peng .

CHEMICAL COMMUNICATIONS, 2010, 46 (26) :4779-4781

[13] Synthesis of Symmetric 1,4-Diamino-2-Butynes via a Cu(I)-Catalyzed One-Pot A3-Coupling/Decarboxylative Coupling of a Propiolic Acid, an Aldehyde, and an Amine [J].

Feng, Huangdi ;

Ermolat'ev, Denis S. ;

Song, Gonghua ;

Van der Eycken, Erik V. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (11) :5149-5154

[14] Synthesis of biaryls via catalytic decarboxylative coupling [J].

Goossen, Lukas J. ;

Deng, Guojun ;

Levy, Laura M. .

SCIENCE, 2006, 313 (5787) :662-664

[15] Synthesis, characterization of palladium hydroxysalen complex and its application in the coupling reaction of arylboronic acids: Mizoroki-Heck type reaction and decarboxylative couplings [J].

Heo, Yumi ;

Kang, Yi Young ;

Palani, Thiruvengadam ;

Lee, Junseong ;

Lee, Sunwoo .

INORGANIC CHEMISTRY COMMUNICATIONS, 2012, 23 :1-5

[16] Copper-Catalyzed C-P Coupling through Decarboxylation [J].

Hu, Jie ;

Zhao, Ning ;

Yang, Bin ;

Wang, Ge ;

Guo, Li-Na ;

Liang, Yong-Min ;

Yang, Shang-Dong .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (20) :5516-5521

[17] Copper-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylates with 1,1-Dibromo-1-alkenes [J].

Huang, Zheng ;

Shang, Rui ;

Zhang, Zi-Rong ;

Tan, Xiao-Dan ;

Xiao, Xiao ;

Fu, Yao .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (09) :4551-4557

[18] Cu-Catalyzed Oxidative Amidation of Propiolic Acids Under Air via Decarboxylative Coupling [J].

Jia, Wei ;

Jiao, Ning .

ORGANIC LETTERS, 2010, 12 (09) :2000-2003

[19] Synthesis and fluorescence of the new environment-sensitive fluorophore 6-chloro-2,3-naphthalimide derivative [J].

Katritzky, Alan R. ;

Ozcan, Sevil ;

Todadze, Ekaterina .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (06) :1296-1300

[20] Palladium-Catalyzed Decarboxylative sp-sp2 Cross-Coupling Reactions of Aryl and Vinyl Halides and Triflates with α,β-Ynoic Acids using Silver Oxide [J].

Kim, Hyunseok ;

Lee, Phil Ho .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (17) :2827-2832

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