Nickel-catalyzed decarboxylative coupling of an alkynyl carboxylic acid with aryl iodides

被引：20

作者：

Son, Yujeong ^{[1
]}

Kim, Han-Sung ^{[1
]}

Lee, Ju-Hyeon ^{[1
]}

Jang, Jisun ^{[1
]}

Lee, Chin-Fa ^{[2
]}

Lee, Sunwoo ^{[1
]}

机构：

[1] Chonnam Natl Univ, Dept Chem, Gwangju 61186, South Korea

[2] Natl Chung Hsing Univ, Dept Chem, Taichung 402, Taiwan

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 14期

基金：

新加坡国家研究基金会;

关键词：

Nickel; Decarboxylative coupling; Alkynyl carboxylic acid; Aryl iodide; Reductant; SONOGASHIRA REACTION; PROPIOLIC ACID; METAL; AMINATION; HALIDES; DIARYLALKYNES; ANNULATION; AMINES; SCOPE;

D O I：

10.1016/j.tetlet.2017.02.073

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A decarboxylative coupling reaction with an alkynyl carboxylic acid and aryl iodides in the presence of a nickel catalyst was developed. When the reaction was conducted with NiCl2 (10 mol%), Xantphos (15 mol Mn (1.0 equiv), and Cs2CO3 (1.5 equiv), the desired diaryl alkynes were formed in moderated to good yields. Furthermore, this method does not produce the diyne, which is formed in the homocoupling of alkynyl carboxylic acids. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：1413 / 1416

页数：4

共 67 条

[41] Copper-Catalyzed Direct Synthesis of Diaryl 1,2-Diketones from Aryl Iodides and Propiolic Acids [J].

Min, Hongkeun ;

Palani, Thiruvengadam ;

Park, Kyungho ;

Hwang, Jinil ;

Lee, Sunwoo .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (13) :6279-6285

[42] One-pot synthesis of diarylalkynes using palladium-catalyzed Sonogashira reaction and decarboxylative coupling of sp carbon and sp2 carbon [J].

Moon, Jeongju ;

Jeong, Miso ;

Nam, Hyungoog ;

Ju, Jinhun ;

Moon, Joong Ho ;

Jung, Hyun Min ;

Lee, Sunwoo .

ORGANIC LETTERS, 2008, 10 (05) :945-948

[43] Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids and Aryl Halides [J].

Moon, Jeongju ;

Jang, Mihee ;

Lee, Sunwoo .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03) :1403-1406

[44]

Negishi E., 2002, Handbook of Organopalladium Chemitry for Organic Synthesis

[45] Palladium-Catalyzed Synthesis of (Z)-3-Arylthioacrylic Acids and Thiochromenones [J].

Palani, Thiruvengadam ;

Park, Kyungho ;

Song, Kwang Ho ;

Lee, Sunwoo .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (06) :1160-1168

[46] Copper-Catalyzed Decarboxylative Three-Component Reactions for the Synthesis of Imidazo[1,2-α]pyridines [J].

Palani, Thiruvengadam ;

Park, Kyungho ;

Kumar, Manian Rajesh ;

Jung, Hyun Ming ;

Lee, Sunwoo .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (26) :5038-5047

[47] Pd-Catalyzed Carbonylative Reactions of Aryl Iodides and Alkynyl Carboxylic Acids via Decarboxylative Couplings [J].

Park, Ahbyeol ;

Park, Kyungho ;

Kim, Yong ;

Lee, Sunwoo .

ORGANIC LETTERS, 2011, 13 (05) :944-947

[48] Transition metal-catalyzed decarboxylative coupling reactions of alkynyl carboxylic acids [J].

Park, Kyungho ;

Lee, Sunwoo .

RSC ADVANCES, 2013, 3 (34) :14165-14182

[49] Metal-Free Decarboxylative Three-Component Coupling Reaction for the Synthesis of Propargylamines [J].

Park, Kyungho ;

Heo, Yumi ;

Lee, Sunwoo .

ORGANIC LETTERS, 2013, 15 (13) :3322-3325

[50] Palladium-Catalyzed Sonogashira Reaction for the Synthesis of Arylalkynecarboxylic Acids from Aryl Bromides at Low Temperature [J].

Park, Kyungho ;

You, Jung-Min ;

Jeon, Seungwon ;

Lee, Sunwoo .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (10) :1973-1978

← 1 2 3 4 5 6 7 →