N‐Heterocyclic Carbene‐Catalyzed Umpolung of Alkynyl 1,2‐Diketones
Authors:
- 17 July 2017
- journal article
- research article
- Published by Wiley in Advanced Synthesis & Catalysis
- Vol. 359 (16) , 2729-2734
Abstract
The umpolung of alkynyl 1,2‐diketones via N‐heterocyclic carbene (NHC) catalysis was achieved for the first time, allowing the rapid access to a large variety of synthetically and pharmaceutically important α‐pyrones under very mild conditions. A completely new NHC‐catalyzed umpolung pattern involving an O‐acylated allenolate as the key intermediate was proposed. Moreover, an unprecedented reaction pathway, featured by a series of group migrations and new bond formation, was postulated to demonstrate the formation of the products. magnified imageKeywords
Funding Information
- Strategic Priority Research Program of the Chinese Academy of Sciences (XDB20000000)
- NSFC (21402199 and 21502192)
- Chinese Recruitment Program of Global Experts
This publication has 73 references indexed in Scilit:
- Employing homoenolates generated by NHC catalysis in carbon–carbon bond-forming reactions: state of the artChemical Society Reviews, 2011
- Extending NHC-Catalysis: Coupling Aldehydes with Unconventional Reaction PartnersAccounts of Chemical Research, 2011
- Organocatalysis by N-Heterocyclic CarbenesChemical Reviews, 2007
- Umpolung Reactivity of Alkenyl Fischer Carbene Complexes, Copper Enolates, and ElectrophilesAngewandte Chemie International Edition, 2006
- Umpolung Reactivity of Alkenyl Fischer Carbene Complexes, Copper Enolates, and ElectrophilesAngewandte Chemie, 2006
- Methods of Reactivity UmpolungAngewandte Chemie International Edition, 1979
- Methoden der ReaktivitätsumpolungAngewandte Chemie, 1979
- Umpolung of the Reactivity of Carbonyl Compounds Through Sulfur-Containing ReagentsSynthesis, 1977
- Umpolung der Reaktivität von Aminen. Nucleophile α‐sek.‐Aminoalkylierung über metallierte NitrosamineAngewandte Chemie, 1975
- Umpolung of Amine Reactivity. Nucleophilic α‐(Secondary Amino)‐alkylation via Metalated NitrosaminesAngewandte Chemie International Edition, 1975