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
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
收藏
页码:1413 / 1416
页数:4
相关论文
共 67 条
[1]   Recent progress and current applications of Sonogashira coupling reaction in water [J].
Bakherad, Mohammad .
APPLIED ORGANOMETALLIC CHEMISTRY, 2013, 27 (03) :125-140
[2]  
Banerjee A., 2013, Nanocatalysis Synthesis and Applications, P133
[3]   Nickel-Catalyzed Monoarylation of Ammonia [J].
Borzenko, Andrey ;
Rotta-Loria, Nicolas L. ;
MacQueen, Preston M. ;
Lavoie, Christopher M. ;
McDonald, Robert ;
Stradiotto, Mark .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (12) :3773-3777
[4]   Porous Polymers Based on Aryleneethynylene Building Blocks [J].
Bunz, Uwe H. F. ;
Seehafer, Kai ;
Geyer, Florian L. ;
Bender, Markus ;
Braun, Ingo ;
Smarsly, Emanuel ;
Freudenberg, Jan .
MACROMOLECULAR RAPID COMMUNICATIONS, 2014, 35 (17) :1466-1496
[5]   RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION [J].
CABRI, W ;
CANDIANI, I .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) :2-7
[6]   Cobalt-Catalyzed Cross-Coupling Reactions [J].
Cahiez, Gerard ;
Moyeux, Alban .
CHEMICAL REVIEWS, 2010, 110 (03) :1435-1462
[7]   Stille Polycondensation for Synthesis of Functional Materials [J].
Carsten, Bridget ;
He, Feng ;
Son, Hae Jung ;
Xu, Tao ;
Yu, Luping .
CHEMICAL REVIEWS, 2011, 111 (03) :1493-1528
[8]   Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds [J].
Cherney, Alan H. ;
Kadunce, Nathaniel T. ;
Reisman, Sarah E. .
CHEMICAL REVIEWS, 2015, 115 (17) :9587-9652
[9]   Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones [J].
Cherney, Alan H. ;
Kadunce, Nathaniel T. ;
Reisman, Sarah E. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (20) :7442-7445
[10]   The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2007, 107 (03) :874-922