Application of Bulky and Electron-Rich MOP-Type Phosphine Ligands in Palladium-Catalyzed α-Arylation of 1,3-Dicarbonyl  Compounds

Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (08): 1410-1415. Previous Articles Next Articles

Original Articles

大位阻、富电子MOP型烷基膦配体在钯催化的1,3-二羰基化合物 α-芳基化反应中的应用

江洪^a; 马芳芳^a ; 谢小敏^a ; 张兆国^*,a,b

(a上海交通大学化学化工学院上海 200240)
(b中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032)

收稿日期:2008-01-14 修回日期:2008-04-01 发布日期:2008-08-18
通讯作者: 张兆国

Application of Bulky and Electron-Rich MOP-Type Phosphine Ligands in Palladium-Catalyzed α-Arylation of 1,3-Dicarbonyl Compounds

JIANG, Hong ^a; MA, Fang-Fang ^a; XIE, Xiao-Min^a ; ZHANG, Zhao-Guo^*,a,b

(aSchool of Chemistry and Chemical Technology, Shanghai Jiaotong University, Shanghai 200240)
(bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry,
Chinese Academy of Sciences, Shanghai 200032)

Received:2008-01-14 Revised:2008-04-01 Published:2008-08-18
Contact: ZHANG, Zhao-Guo

Abstract

Bulky and electron-rich MOP-type phosphine ligand 2-ditertbutylphosphino-2’-isopropyloxy-　1,1’-binaphthyl (L1) shows good catalytic activity in palladium-catalyzed α-arylation of 1,3-dicarbonyl compounds. Base played a crucial role in this reaction: in the Pd(OAc)2/L1 catalyzed α-arylation of ethyl malonate, K3PO4 is the base of choice; in the α-arylation of ethyl acetoacetate, K2CO3 is the most effective base. For the α-arylation of ethyl acetoacetate, the product was α-aryl ethyl acetoacetates, rather than ethyl α-arylacetates which are the major products in other catalytic systems.

Key words: palladium-catalysis, aryl halide, phosphine, α-arylation

Cite this article

JIANG, Hong ^a; MA, Fang-Fang ^a; XIE, Xiao-Min^a ; ZHANG, Zhao-Guo^*,a,b. Application of Bulky and Electron-Rich MOP-Type Phosphine Ligands in Palladium-Catalyzed α-Arylation of 1,3-Dicarbonyl Compounds[J]. Chin. J. Org. Chem., 2008, 28(08): 1410-1415.

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大位阻、富电子MOP型烷基膦配体在钯催化的1,3-二羰基化合物 α-芳基化反应中的应用

Application of Bulky and Electron-Rich MOP-Type Phosphine Ligands in Palladium-Catalyzed α-Arylation of 1,3-Dicarbonyl Compounds

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