Selective synthesis of (E)-triethyl(2-arylethenyl)silane derivatives by reaction of aryl bromides with triethyl vinylsilane catalysed by a palladium-tetraphosphine complex

被引:24
作者
Battace, A
Zair, T
Doucet, H
Santelli, M
机构
[1] CNRS, UMR 6180, Synth Organ Lab, F-13397 Marseille, France
[2] Univ Aix Marseille 3, Fac Sci St Jerome, F-13397 Marseille, France
[3] Univ Moulay Ismail, Fac Sci, Lab Chim Organ Appl, Meknes 50000, Morocco
关键词
tetraphosphine; palladium; Heck-vinylation; vinyl silanes; aryl bromides;
D O I
10.1016/j.jorganchem.2005.05.014
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Cis, cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane/0.5[PdCI(C3H5)](2) system catalyses the Heck reaction of vinylsilane derivatives with a range of aryl bromides with high ratio substrate/catalyst in good yields. The formation of mixtures of styrene, (E)-triethyl(2-arylethenyl)sitane and triethyl(1-arylethenyl)silane derivatives was observed in some cases. Very high selectivities (up to 100%) in favour of the formation of (E)-triethyl(2-arylethenyl)silane derivatives were obtained in the presence of sodium acetate as base. With other bases such as potassium carbonate, the formation of large amounts of styrene derivatives was observed. The reaction tolerates several functions such as fluoro, trifluoromethyl, methoxy, dimethylamino, acetyl, formyl, benzoyl, carboxylate, nitro or nitrile. Moreover, turnover numbers up to 10,000 can be obtained for this reaction. (c) 2005 Elsevier B.V. All rights reserved.
引用
收藏
页码:3790 / 3802
页数:13
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