Copper-Free Oxime-Palladacycle-Catalyzed Sonogashira Alkynylation of Deactivated Aryl Bromides and Chlorides in Water under Microwave Irradiation

被引：27
作者：
Buxaderas, Eduardo [1 ,2 ]
Alonso, Diego A. [1 ,2 ]
Najera, Carmen [1 ,2 ]
机构：
[1] Univ Alicante, Dept Quim Organ, Alicante 03690, Spain
[2] Univ Alicante, Inst Sintesis Organ, Alicante 03690, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 26期
关键词：
Cross-coupling; Microwave chemistry; Palladium; Aryl halides; Alkynes; CROSS-COUPLING REACTIONS; TERMINAL ALKYNES; AQUEOUS-MEDIA; PALLADIUM; DIMERIZATION; SUZUKI; IMIDAZOLYLSULFONATES; COMPLEXES; HECK;
D O I：
10.1002/ejoc.201300785
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Palladium-catalyzed Heck alkynylation cross-coupling reactions between terminal alkynes and deactivated aryl chlorides and aryl bromides can be performed in the absence of copper cocatalyst with water as solvent at 130 degrees C under microwave irradiation. An oxime-derived chloro-bridged palladacycle is an efficient precatalyst for this transformation with 2-dicyclohexylphosphanyl-2,4,6-triisopropylbiphenyl (XPhos) as ancillary ligand, pyrrolidine as base, and SBDS as surfactant. All of the reactions can be performed under air and with reagent-grade chemicals under low loading conditions (0.1-1 mol-% Pd).
引用
收藏
页码：5864 / 5870
页数：7
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