Copper-Free Heck-Cassar-Sonogashira and Suzuki-Miyaura Reactions of Aryl Chlorides: A Sustainable Approach

被引：4
|
作者：
Palladino, Chiara [1 ]
Fantoni, Tommaso [1 ]
Ferrazzano, Lucia [1 ]
Tolomelli, Alessandra [1 ]
Cabri, Walter [1 ]
机构：
[1] Univ Bologna, Ctr Chem Catalysis, Dept Chem Giacomo Ciamician, Tolomelli Cabri Lab, I-40126 Bologna, Italy
来源：
ACS SUSTAINABLE CHEMISTRY & ENGINEERING | 2023年 / 11卷 / 44期
关键词：
copper-free Heck-Cassar-Sonogashira; Suzuki-Miyaura; palladium; green solvents; aryl chlorides; COUPLING REACTIONS; CROSS-COUPLINGS; PHARMACEUTICAL-INDUSTRY; GREEN CHEMISTRY; C-C; PALLADIUM; CATALYSTS; PERSPECTIVE; EFFICIENT; LIGAND;
D O I：
10.1021/acssuschemeng.3c04926
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Sustainable and efficient aryl halides with copper-free Heck-Cassar-Sonogashira (HCS) and Suzuki-Miyaura (SM) cross-coupling reactions were described. Independently from the aryl chloride substituents, the green protocol based on N-hydroxyethylpyrrolidone (HEP)/water as solvents and sodium 2 '-dicyclohexylphosphino-2,6-dimethoxy-1,1 '-biphenyl-3-sulfonate (sSPhos) as ligand afforded the target products with a high turnover number (TON), high reaction mass efficiency (RME), and low process mass intensity (PMI). The best results have been obtained with TMG and Cs2CO3 as the base for the HCS and Cs2CO3 and K2CO3 for the SM coupling. The PMI and RME achieved are among the best in the field and allowed us to simplify purification processes that are critical for industrial applications.
引用
收藏
页码：15994 / 16004
页数：11
相关论文
共 50 条
  • [1] New Mechanistic Insights into the Copper-Free Heck-Cassar-Sonogashira Cross-Coupling Reaction
    Palladino, Chiara
    Fantoni, Tommaso
    Ferrazzano, Lucia
    Muzzi, Beatrice
    Ricci, Antonio
    Tolomelli, Alessandra
    Cabri, Walter
    ACS CATALYSIS, 2023, 13 (18): : 12048 - 12061
  • [2] PEG Click-Triazole Palladacycle: An Efficient Precatalyst for Palladium-Catalyzed Suzuki-Miyaura and Copper-free Sonogashira Reactions in Neat Water
    Zhang, Guofu
    Zhang, Wei
    Luan, Yuxin
    Han, Xingwang
    Ding, Chengrong
    CHINESE JOURNAL OF CHEMISTRY, 2015, 33 (07) : 705 - 710
  • [3] Resorcinarenyl-Phosphines in Suzuki-Miyaura CrossCoupling Reactions of Aryl Chlorides
    Monnereau, Laure
    El Moll, Hani
    Semeril, David
    Matt, Dominique
    Toupet, Loic
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2014, 2014 (08) : 1364 - 1372
  • [4] Palladium-Catalyzed Suzuki-Miyaura Coupling Reactions of Boronic Acid Derivatives with Aryl Chlorides
    Zhou, Zihong
    Zhang, Yaqi
    Xia, Wang
    Chen, Huixuan
    Liang, Hao
    He, Xuefeng
    Yu, Sifan
    Cao, Rihui
    Qiu, Liqin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (10) : 1260 - 1268
  • [5] Efficient Suzuki-Miyaura coupling reactions between lithium alkynyltrimethylborates and aryl chlorides
    Torres, GH
    Choppin, S
    Colobert, F
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (06) : 1450 - 1454
  • [6] Sunlight promoted palladium catalysed Mizoroki-Heck, Suzuki-Miyaura and Sonogashira reactions
    Chaudhary, Anju R.
    Bedekar, Ashutosh V.
    TETRAHEDRON LETTERS, 2012, 53 (45) : 6100 - 6103
  • [7] Palladium Supported on a Polyionic Resin as an Efficient, Ligand-Free, and Recyclable Catalyst for Heck, Suzuki-Miyaura, and Sonogashira Reactions
    Basu, Basudeb
    Das, Sajal
    Das, Pralay
    Mandal, Bablee
    Banerjee, Dipanjan
    Almqvist, Fredrik
    SYNTHESIS-STUTTGART, 2009, (07): : 1137 - 1146
  • [8] General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water
    Anderson, KW
    Buchwald, SL
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) : 6173 - 6177
  • [9] A Highly Active Heterogeneous Palladium Catalyst for the Suzuki-Miyaura and Ullmann Coupling Reactions of Aryl Chlorides in Aqueous Media
    Yuan, Bizhen
    Pan, Yingyi
    Li, Yingwei
    Yin, Biaolin
    Jiang, Huanfeng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (24) : 4054 - 4058
  • [10] Polystyrene supported thiopseudourea Pd(II) complex: Applications for Sonogashira, Suzuki-Miyaura, Heck, Hiyama and Larock heteroannulation reactions
    Keesara, Srinivas
    Parvathaneni, Saiprathima
    Dussa, Govardhan
    Mandapati, Mohan Rao
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2014, 765 : 31 - 38
12345