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  Facile N9-Alkylation of Xanthine Derivatives and Their Use as Precursors for N-Heterocyclic Carbene Complexes

Mokfi, M., Rust, J., Lehmann, C. W., & Mohr, F. (2021). Facile N9-Alkylation of Xanthine Derivatives and Their Use as Precursors for N-Heterocyclic Carbene Complexes. Molecules, 26(12): 3705. doi:10.3390/molecules26123705.

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 Creators:
Mokfi, Moloud1, Author
Rust, Jörg2, Author              
Lehmann, Christian W.2, Author              
Mohr, Fabian1, Author
Affiliations:
1Faculty of Mathematics and Natural Sciences, Inorganic Chemistry, Bergische University Wuppertal, 42119 Wuppertal, Germany, ou_persistent22              
2Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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Free keywords: xanthines; N-heterocyclic carbenes; X-ray structures
 Abstract: The xanthine-derivatives 1,3,7-trimethylxanthine, 1,3-dimethyl-7-benzylxanthine and 1,3-dimethyl-7-(4-chlorobenzyl)xanthine are readily ethylated at N9 using the cheap alkylating agents ethyl tosylate or diethyl sulfate. The resulting xanthinium tosylate or ethyl sulfate salts can be converted into the corresponding PF6 and chloride salts. The reaction of these xanthinium salts with silver(I) oxide results in the formation of different silver(I) carbene-complexes. In the presence of ammonia, ammine complexes [Ag(NHC)(NH3)]PF6 are formed, whilst with Et2NH, the bis(carbene) salts [Ag(NHC)2]PF6 were isolated. Using the xanthinium chloride salts neutral silver(I) carbenes [Ag(NHC)Cl] were prepared. These silver complexes were used in a variety of transmetallation reactions to give the corresponding gold(I), ruthenium(II) as well as rhodium(I) and rhodium(III) complexes. The compounds were characterized by various spectroscopic methods as well as X-ray diffraction.

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Language(s): eng - English
 Dates: 2021-05-282021-06-152021-06-17
 Publication Status: Published online
 Pages: 17
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.3390/molecules26123705
 Degree: -

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Title: Molecules
Source Genre: Journal
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Publ. Info: Basel : MDPI
Pages: - Volume / Issue: 26 (12) Sequence Number: 3705 Start / End Page: - Identifier: ISSN: 1420-3049
CoNE: https://pure.mpg.de/cone/journals/resource/954925623244