Synthesis of functionalized alkynes via palladium-catalyzed Sonogashira reactions

被引：12
|
作者：
Ibrahim, Mansur B. [1 ]
El Ali, Bassam [1 ]
Malik, Imran [1 ]
Fettouhi, Mohammed [1 ]
机构：
[1] King Fahd Univ Petr & Minerals, Dept Chem, Dhahran 31261, Saudi Arabia
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 05期
关键词：
Palladium-bis(oxazoline); Sonogashira coupling; Diiodobenzene; Alkyl alkynes; Dialkynes; CROSS-COUPLING REACTIONS; COPPER-FREE; ARYL BROMIDES; SUZUKI-MIYAURA; TERMINAL ALKYNES; EFFICIENT; HECK; CHLORIDES; COMPLEX; LIGAND;
D O I：
10.1016/j.tetlet.2015.12.086
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly efficient protocol for the copper and phosphine free Sonogashira cross-coupling reactions of aryl iodides with terminal alkynes under aerobic conditions has been developed. Using 1 mol % of the palladium-bis(oxazoline) complex, Pd-BOX A, in the presence of KOH, and a CH3CN-H2O solvent system allowed for the cross -coupling reactions to proceed at room temperature or 60 degrees C. This new catalytic system was found to be highly active for the cross-coupling reaction of aryl diiodo substrates with unactivated alkyl alkynes to produce various symmetrical dialkynes, as well as for the cross -coupling of terminal dialkynes with aryl iodides to generate symmetrical disubstituted internal alkynes. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：554 / 558
页数：5
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