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Discovering the Site-Selective Umpolung of Ketones Triggered by Hypervalent Fluoro-Iodanes – Why Investigating Side Reactions Matters!
- Source :
-
Synlett . Mar2023, Vol. 34 Issue 5, p405-413. 9p. - Publication Year :
- 2023
-
Abstract
- In this account, we describe our journey leading to the discovery of a generally applicable umpolung method for the α-functionalization of ketones. Central to this reaction is the cyclic hypervalent fluoro-iodane, which is mostly known for various alkene functionalizations enabling, for example, the synthesis of fluoro-benzoxazepines, indoles, and ketones. During this work, we encountered α-functionalized ketones as minor side products. This observation prompted us to further investigate this reactivity, thus revealing a directed umpolung of pyridyl ketones by the fluoro-iodane. The key to the success was the unexpected non-covalent interaction between the nucleophile, substrate, and iodane. 1 Introduction 2 Cyclizations Triggered by the Fluorination of Styrenes 3 Umpolung Reactions Facilitated by Hypervalent Iodanes 4 Discovering and Evolving a Fluoro-Iodane-Triggered Regioselective α-Functionalization of Carbonyl Compounds 5 First Investigations on the Nitrogen-Directed Umpolung 6 Conclusion [ABSTRACT FROM AUTHOR]
- Subjects :
- *UMPOLUNG
*KETONES
*CARBONYL compounds
*FLUORINATION
*ALKENES
Subjects
Details
- Language :
- English
- ISSN :
- 09365214
- Volume :
- 34
- Issue :
- 5
- Database :
- Academic Search Index
- Journal :
- Synlett
- Publication Type :
- Academic Journal
- Accession number :
- 162114340
- Full Text :
- https://doi.org/10.1055/a-1990-5495