Green and Scalable Palladium-on-Carbon-Catalyzed Tsuji-Trost Coupling Reaction Using an Efficient and Continuous Flow System

被引:10
作者
Cazorla, Clement [1 ]
Billamboz, Muriel [2 ]
Bricout, Herve [3 ]
Monflier, Eric [3 ]
Len, Christophe [1 ]
机构
[1] Univ Technol Compiegne, Sorbonne Univ, Ctr Rech Royallieu, CS 60 319, F-60203 Compiegne, France
[2] Ecole Super Chim Organ & Minerale, 1 Allee Reseau Jean Marie Buckmaster, F-60200 Compiegne, France
[3] Univ Artois, Univ Lille, Ecole Natl Super Chim Lille, UCCS,UMR 8181,CNRS,Cent Lille, F-62300 Lens, France
关键词
Cross-coupling; Flow chemistry; Allylic compounds; Green chemistry; Palladium; SUZUKI-MIYAURA REACTION; LIGAND-FREE; SUPPORTED PALLADIUM; ALLYLIC SUBSTITUTION; HIGHLY EFFICIENT; SOLAR-CELLS; HECK; MICROWAVE; REACTORS; 5-IODO-2'-DEOXYURIDINE;
D O I
10.1002/ejoc.201601311
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first continuous flow Tsuji-Trost coupling reaction between allylic compounds and various nucleophiles has been successfully achieved within only around 40 s during a single pass through a cartridge filled with palladium on carbon (Pd/C). Two methods have been designed by using the H-cube ThalesNano technology that enable the efficient production of added-value compounds on the gram scale with high productivity. Under the optimized conditions, the cartridge catalyst can be used for 60 min of continuous processing without a decrease in reactivity. A large range of substrates and nucleophiles have successfully been submitted to the standard methods, giving good-to-excellent yields and productivity.
引用
收藏
页码:1078 / 1085
页数:8
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