Sonogashira coupling reactions with ligand-free heterogeneous nanoporous Pd catalyst

被引:1
作者
Zhang, Chuting [1 ]
Peng, Lijuan [1 ]
Song, Bohou [1 ]
Li, Zhiwen [1 ]
Cao, Xiaoqun [1 ]
机构
[1] Shandong First Med Univ & Shandong Acad Med Sci, Sch Chem & Pharmaceut Engn, Tai An 271016, Peoples R China
关键词
Nanoporous palladium; Sonogashira cross-coupling reaction; C-C bond; Aryl alkynes; PALLADIUM;
D O I
10.1016/j.inoche.2023.111471
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The Sonogashira coupling reaction is one of the most important protocols for the production of aryl alkynes. In order to solve the problems existing in Sonogashira cross-coupling reaction, according to the application of nanoporous palladium in Suzuki and Heck cross-coupling reactions, nanoporous palladium was used as the sustainable catalyst for the Sonogashira cross-coupling reaction. A sustainable catalyst system was tested and optimized without cuprous ion, phosphine ligand, or amine additives. Nanoporous palladium catalyst remained stable over five cycles without significant leaching or loss of catalytic activity, and the desired alkynes were obtained in high yields.
引用
收藏
页数:5
相关论文
共 50 条
[31]   Synthesis of Pharmacologically Relevant New Derivatives of Maleimides via Ligand-Free Pd-Catalyzed Suzuki–Miyaura Cross-Coupling Reactions [J].
Muhammad Sharif ;
Julita Opalach ;
Ralf Jackstell ;
Anahit Pews-Davtyan ;
Matthias Beller .
Arabian Journal for Science and Engineering, 2020, 45 :4717-4725
[32]   Pd/C as a highly active catalyst for Heck, Suzuki and Sonogashira reactions [J].
Heidenreich, RG ;
Köhler, K ;
Krauter, JGE ;
Pietsch, J .
SYNLETT, 2002, (07) :1118-1122
[33]   Ni2O3-around-Pd hybrid on graphene oxide: An efficient catalyst for ligand-free Suzuki-Miyaura coupling reaction [J].
Nie, Renfeng ;
Shi, Juanjuan ;
Du, Weichen ;
Hou, Zhaoyin .
APPLIED CATALYSIS A-GENERAL, 2014, 473 :1-6
[34]   Palladium on charcoal-catalyzed ligand-free Stille coupling [J].
Yabe, Yuki ;
Maegawa, Tomohiro ;
Monguchi, Yasunari ;
Sajiki, Hironao .
TETRAHEDRON, 2010, 66 (45) :8654-8660
[35]   Ligand-free palladium-catalyzed decarboxylative coupling reactions of aryl iodides and alkynyl carboxylic acids [J].
Pyo, Ayoung ;
Kim, Ji Dang ;
Choi, Hyun Chul ;
Lee, Sunwoo .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2013, 724 :271-274
[36]   Copper- and ligand-free Sonogashira reaction catalyzed by palladium in microemulsion: Effects of surfactant and alcohol [J].
Jiang, Jian-Zhong ;
Wei, Yan-An ;
Cai, Chun .
JOURNAL OF COLLOID AND INTERFACE SCIENCE, 2007, 312 (02) :439-443
[37]   Pd/C: An Efficient, Heterogeneous and Reusable Catalyst for Phosphane-Free Carbonylative Suzuki Coupling Reactions of Aryl and Heteroaryl Iodides [J].
Khedkar, Mayur V. ;
Tambade, Pawan J. ;
Qureshi, Ziyauddin S. ;
Bhanage, Bhalchandra M. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (36) :6981-6986
[38]   Ligand-Free and Heterogeneous Palladium on Carbon-Catalyzed Hetero-Suzuki-Miyaura Cross-Coupling [J].
Kitamura, Yoshiaki ;
Sako, Satoko ;
Tsutsui, Azusa ;
Monguchi, Yasunari ;
Maegawa, Tomohiro ;
Kitade, Yukio ;
Sajiki, Hironao .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (04) :718-730
[39]   Synthesis of Pharmacologically Relevant New Derivatives of Maleimides via Ligand-Free Pd-Catalyzed Suzuki-Miyaura Cross-Coupling Reactions [J].
Sharif, Muhammad ;
Opalach, Julita ;
Jackstell, Ralf ;
Pews-Davtyan, Anahit ;
Beller, Matthias .
ARABIAN JOURNAL FOR SCIENCE AND ENGINEERING, 2020, 45 (06) :4717-4725
[40]   Ligand-free Pd-Catalyzed C-N Coupling of Diphenylamine and Aryl Halides under Air [J].
Zhang Binbin ;
Zhan Dan ;
Zhang Xiaoping ;
Xiang Qinjie ;
Zeng Qingle .
ACTA CHIMICA SINICA, 2012, 70 (15) :1655-1659