Christoph J. Vonnemann, Dr. Elric Engelage, Dr. Jas S. Ward, Prof. Dr. Kari Rissanen, Prof. Dr. Sandro Keller, Prof. Dr. Stefan M. Huber
{"title":"Ortho-Carborane-Derived Halogen Bonding Organocatalysts","authors":"Christoph J. Vonnemann, Dr. Elric Engelage, Dr. Jas S. Ward, Prof. Dr. Kari Rissanen, Prof. Dr. Sandro Keller, Prof. Dr. Stefan M. Huber","doi":"10.1002/anie.202424072","DOIUrl":null,"url":null,"abstract":"<p>Multidentate neutral halogen bonding catalysts based on iodinated icosahedral <i>ortho</i>-carborane moieties are introduced. Co-crystallization-studies, calorimetric measurements, and <sup>1</sup>H NMR titrations demonstrate their strong binding to halides and neutral compounds, further underlined by quantum-chemical calculations. Thus, their superior Lewis acidity compared to traditional perfluorinated halogen-bond donors has been shown. The iodocarborane catalysts also outperformed the latter in a halide abstraction reaction and catalyzed a nitro-Michael addition reaction, which was previously out of reach for neutral halogen-bonding-based organocatalysts.</p>","PeriodicalId":125,"journal":{"name":"Angewandte Chemie International Edition","volume":"64 17","pages":""},"PeriodicalIF":16.9000,"publicationDate":"2025-02-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/anie.202424072","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Angewandte Chemie International Edition","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/anie.202424072","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Multidentate neutral halogen bonding catalysts based on iodinated icosahedral ortho-carborane moieties are introduced. Co-crystallization-studies, calorimetric measurements, and 1H NMR titrations demonstrate their strong binding to halides and neutral compounds, further underlined by quantum-chemical calculations. Thus, their superior Lewis acidity compared to traditional perfluorinated halogen-bond donors has been shown. The iodocarborane catalysts also outperformed the latter in a halide abstraction reaction and catalyzed a nitro-Michael addition reaction, which was previously out of reach for neutral halogen-bonding-based organocatalysts.
期刊介绍：
Angewandte Chemie, a journal of the German Chemical Society (GDCh), maintains a leading position among scholarly journals in general chemistry with an impressive Impact Factor of 16.6 (2022 Journal Citation Reports, Clarivate, 2023). Published weekly in a reader-friendly format, it features new articles almost every day. Established in 1887, Angewandte Chemie is a prominent chemistry journal, offering a dynamic blend of Review-type articles, Highlights, Communications, and Research Articles on a weekly basis, making it unique in the field.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
