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

页码：5864 / 5870

页数：7

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