Knappke, Christiane E. I., Arduengo, Anthony J., III, Jiao, Haijun, Neudoerfl, Joerg-Martin and Jacobi von Wangelin, Axel (2011). On the Dual Role of N-Heterocyclic Carbenes as Bases and Nucleophiles in Reactions with Organic Halides. Synthesis (23). S. 3784 - 3796. STUTTGART: GEORG THIEME VERLAG KG. ISSN 1437-210X

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Abstract

The synthetic consequences of different basicities, nucleophilicities, and sterics of N-heterocyclic carbenes have been studied in reactions of imidazolin-2-ylidenes with organic halides. Highly nucleophilic and less basic carbenes cleanly gave alkylideneimidazolines, the deoxy analogues of Breslow-type intermediates. More basic NHCs engaged in unwanted deprotonation or dehydrohalogenation reactions.

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Knappke, Christiane E. I.UNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Arduengo, Anthony J., IIIUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Jiao, HaijunUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Neudoerfl, Joerg-MartinUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Jacobi von Wangelin, AxelUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
URN: urn:nbn:de:hbz:38-484970
DOI: 10.1055/s-0031-1289593
Journal or Publication Title: Synthesis
Number: 23
Page Range: S. 3784 - 3796
Date: 2011
Publisher: GEORG THIEME VERLAG KG
Place of Publication: STUTTGART
ISSN: 1437-210X
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
DIELS-ALDER REACTION; IMIDAZOLE DERIVATIVES; STABLE CARBENES; OLEFIN; SALTS; COORDINATION; UMPOLUNG; BASICITY; 2-ALKYLIDENEIMIDAZOLIDINES; ALKYLATIONMultiple languages
Chemistry, OrganicMultiple languages
URI: http://kups.ub.uni-koeln.de/id/eprint/48497

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