Pd(II) complexes of monodentate deoxycholic acid derived binaphthyl diamido phosphites as chiral catalysts in the asymmetric Suzuki-Miyaura cross-coupling

Q2 Chemistry Tetrahedron, asymmetry Pub Date : 2017-11-15 DOI:10.1016/j.tetasy.2017.09.012
Grazia Iannucci , Vincenzo Passarelli , Alessandro Passera , Anna Iuliano
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引用次数: 5

Abstract

Chiral binaphthyl diamidophosphites derived from deoxycholic acid were synthesized and used as ligands for the preparation of mononuclear Pd(II) complexes, which were employed as catalysts in the asymmetric Suzuki-Miyaura cross-coupling of arylboronic acids with aryl bromides. Among the different reaction parameters, the substrate concentration emerged as being crucial for the outcome of the reaction: the reaction was faster in a concentrated reaction mixture, and could be performed at 0 °C, where the reaction promoted by the Pd-complexes was more enantioselective affording cross-coupling products with ee up to 70%.

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Pd(II)配合物在不对称Suzuki-Miyaura交叉偶联中的手性催化作用
以去氧醛酸为原料合成了手性二磷二亚磷酸酯,并以其为配体制备单核Pd(II)配合物,作为催化剂催化芳基硼酸与芳基溴化物的不对称Suzuki-Miyaura交偶联反应。在不同的反应参数中,底物浓度对反应结果至关重要:在浓缩的反应混合物中反应速度更快,可以在0°C下进行,其中pd配合物促进的反应更具对映选择性,可提供ee高达70%的交叉偶联产物。
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来源期刊
Tetrahedron, asymmetry
Tetrahedron, asymmetry 化学-无机化学与核化学
CiteScore
4.70
自引率
0.00%
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0
审稿时长
1 months
期刊介绍: Cessation. Tetrahedron: Asymmetry presents experimental or theoretical research results of outstanding significance and timeliness on asymmetry in organic, inorganic, organometallic and physical chemistry, as well as its application to related disciplines, especially bio-organic chemistry. The journal publishes critical reviews, original research articles and preliminary communications dealing with all aspects of the chemical, physical and theoretical properties of non-racemic organic and inorganic materials and processes. Topics relevant to the journal include: the physico-chemical and biological properties of enantiomers; strategies and methodologies of asymmetric synthesis; resolution; chirality recognition and enhancement; analytical techniques for assessing enantiomeric purity and the unambiguous determination of absolute configuration; and molecular graphics and modelling methods for interpreting and predicting asymmetric phenomena. Papers describing the synthesis or properties of non-racemic molecules will be required to include a separate statement in the form of a Stereochemistry Abstract, for publication in the same issue, of the criteria used for the assignment of configuration and enantiomeric purity.
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