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
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