Pd(II)配合物在不对称Suzuki-Miyaura交叉偶联中的手性催化作用

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
{"title":"Pd(II)配合物在不对称Suzuki-Miyaura交叉偶联中的手性催化作用","authors":"Grazia Iannucci ,&nbsp;Vincenzo Passarelli ,&nbsp;Alessandro Passera ,&nbsp;Anna Iuliano","doi":"10.1016/j.tetasy.2017.09.012","DOIUrl":null,"url":null,"abstract":"<div><p><span>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</span> <!-->°C, where the reaction promoted by the Pd-complexes was more enantioselective affording cross-coupling products with ee up to 70%.</p></div>","PeriodicalId":22237,"journal":{"name":"Tetrahedron, asymmetry","volume":"28 11","pages":"Pages 1618-1625"},"PeriodicalIF":0.0000,"publicationDate":"2017-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.09.012","citationCount":"5","resultStr":"{\"title\":\"Pd(II) complexes of monodentate deoxycholic acid derived binaphthyl diamido phosphites as chiral catalysts in the asymmetric Suzuki-Miyaura cross-coupling\",\"authors\":\"Grazia Iannucci ,&nbsp;Vincenzo Passarelli ,&nbsp;Alessandro Passera ,&nbsp;Anna Iuliano\",\"doi\":\"10.1016/j.tetasy.2017.09.012\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p><span>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</span> <!-->°C, where the reaction promoted by the Pd-complexes was more enantioselective affording cross-coupling products with ee up to 70%.</p></div>\",\"PeriodicalId\":22237,\"journal\":{\"name\":\"Tetrahedron, asymmetry\",\"volume\":\"28 11\",\"pages\":\"Pages 1618-1625\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2017-11-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1016/j.tetasy.2017.09.012\",\"citationCount\":\"5\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron, asymmetry\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0957416617303610\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"Chemistry\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron, asymmetry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0957416617303610","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Chemistry","Score":null,"Total":0}
引用次数: 5

摘要

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。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

摘要图片

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
Pd(II) complexes of monodentate deoxycholic acid derived binaphthyl diamido phosphites as chiral catalysts in the asymmetric Suzuki-Miyaura cross-coupling

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%.

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
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%
发文量
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.
期刊最新文献
Graphical contents list Editorial board Contributors to this issue Nucleophilic substitution at phosphorus: stereochemistry and mechanisms Enantioselective synthesis of chiral 4H-pyran derivatives through [3+3] tandem reaction over a squaramide catalyst
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1