Direct synthesis of protected arylacetaldehydes by tetrakis(phosphane)palladium-catalyzed arylation of ethyleneglycol vinyl ether

被引:21
作者
Kondolff, I
Doucet, H
Santelli, M
机构
[1] CNRS, UMR 6180, F-13397 Marseille 20, France
[2] Univ Aix Marseille 3, Lab Synth Organ, Fac Sci St Jerome, F-13397 Marseille 20, France
关键词
aryl halides; arylacetaldehydes; homogeneous catalysis; palladium; phosphane ligands;
D O I
10.1002/ejoc.200500540
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A range of aryl bromides undergo Heck reaction with ethylene glycol vinyl ether, in the presence of [PdCl(C3H5)](2)/ cis,cis,cis-1,2,3,4-tetrakis [(diphenylphosphanyl)methyl]cyclopentane as catalyst, to give regioselectively protected arylacetaldehydes in good yields. The beta-arylation products were obtained in with 93-100% selectivity with electron-poor aryl bromides or heteroaryl bromides. Furthermore, this catalyst can be used at low loading, even for reactions with sterically hindered aryl bromides. The aryl vinyl ether intermediates undergo subsequent ketalisation to give the corresponding 2-benzyl,-1,3-dioxolane derivatives. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).
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页码:765 / 774
页数:10
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