in the repository
URN to cite this document: urn:nbn:de:bvb:703-epub-9078-8
Title data
Maiti, Rakesh ; Cauwenbergh, Robin ; Nath, Aritra ; Guimarães, Ana B. R. ; Qin, Yuman ; Maseras, Feliu ; Das, Shoubhik:
EDA Complex-Driven Desaturation of Heterocyclic Carbonyl Compounds Enabled by HFIP.
In: Angewandte Chemie International Edition.
Vol. 64
(2025)
Issue 49
.
- e202514539.
ISSN 1521-3773
DOI der Verlagsversion: https://doi.org/10.1002/anie.202514539
![[thumbnail of Angew Chem Int Ed - 2025 - Maiti - EDA Complex‐Driven Desaturation of Heterocyclic Carbonyl Compounds Enabled by HFIP.pdf]](https://epub.uni-bayreuth.de/style/images/fileicons/application_pdf.png) |
|
||||||||
|
Download (1MB)
|
Project information
| Project title: |
Project's official title Project's id Open Access Publizieren No information |
|---|
Abstract
Recently, electron donor–acceptor (EDA) complex-mediated organic synthetic strategies have emerged as powerful tools for diverse bond-forming transformations; however, their efficiency often diminishes when ionic reactants are involved. This limitation arises from the requirement of polar solvents such as DMSO or DMF to solubilize ionic species for the formation of effective EDA complex. Consequently, these solvents engage in competing EDA complex formation or disrupt ionization equilibria. In parallel, there is a pressing necessity of modern and efficient strategy to achieve dehydrogenation reactions, which are in general limited by the drawbacks of traditional approaches. To address both, herein, we disclose an innovative desaturation strategy based on the formation of an EDA complex between a dihydrogenated organic substrate and an N-methoxy pyridinium salt. In our study, solubility issues, which are associated with the pyridinium salt, are effectively addressed by using hexafluoroisopropanol (HFIP). Beyond enhancing solubility, HFIP also functions as a transient H-shuttle, significantly reducing the activation energy for this transformation. This cooperative interplay between HFIP and the pyridinium salt enables the efficient and selective desaturation of a broad range of heterocyclic carbonyl compounds—including quinolinones, coumarins, and flavones—which are valuable scaffolds in pharmaceutical and agrochemical research. At the end, detailed mechanistic studies with the aid of experiments as well as DFT studies clearly disclose the mechanism as well as the important role of HFIP in this reaction.
Further data
| Item Type: | Article in a journal |
|---|---|
| Keywords: | Dehydrogenation; EDA-complex; Heterocyclic carbonyls; DFT; Sustainable protocol |
| DDC Subjects: | 500 Science > 540 Chemistry |
| Institutions of the University: | Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Organic Chemistry I - Photo- und Elektrokatalyse für Nachhaltigkeit > Chair Organic Chemistry I - Photo- und Elektrokatalyse für Nachhaltigkeit - Univ.-Prof. Dr. Shoubhik Das Faculties Faculties > Faculty of Biology, Chemistry and Earth Sciences Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Organic Chemistry I - Photo- und Elektrokatalyse für Nachhaltigkeit |
| Language: | English |
| Originates at UBT: | Yes |
| URN: | urn:nbn:de:bvb:703-epub-9078-8 |
| Date Deposited: | 07 Apr 2026 07:40 |
| Last Modified: | 07 Apr 2026 07:40 |
| URI: | https://epub.uni-bayreuth.de/id/eprint/9078 |
Download Statistics