Reactions of 1-Alkyl-3-phenylbenzimidazolium Salts with Ag<sub>2</sub>O: The Formation of a Ring-Opening Formamide Derivative and a Ag Complex with an <i>N</i>-heterocyclic Carbene Ligand
This study investigated the reactions of 1-alkyl-3-phenylbenzimidazolium salts with Ag<sub>2</sub>O. It was found that the selectivity of the reaction products was influenced by the <i>N</i>-alkyl substituent on the azolium ring. For example, treating 1-methyl-3-phenylbenzimi...
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| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-01-01
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| Series: | Inorganics |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2304-6740/13/1/18 |
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| Summary: | This study investigated the reactions of 1-alkyl-3-phenylbenzimidazolium salts with Ag<sub>2</sub>O. It was found that the selectivity of the reaction products was influenced by the <i>N</i>-alkyl substituent on the azolium ring. For example, treating 1-methyl-3-phenylbenzimidazolium iodide (<b>2</b>) with Ag<sub>2</sub>O for 24 h produced the ring-opening formamide derivative <i>N</i>-[2-(phenylamino)phenyl]-<i>N</i>-methylformamide (<b>2b</b>) in an 85% yield. In contrast, the reaction of 1-benzyl-3-phenylbenzimidazolium chloride (<b>3</b>) with Ag<sub>2</sub>O under the same conditions yielded the corresponding <i>N</i>-heterocyclic carbene (NHC)–Ag complex (1-benzyl-3-phenylbenzimidazol-2-ylidene) silver(I) chloride (<b>3a</b>) in an 86% yield. Furthermore, the corresponding monodentate NHC–Au complex <b>2c</b> could be synthesized by allowing <b>2</b> to react with AuCl(SMe<sub>2</sub>) in the presence of Ag<sub>2</sub>O. |
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| ISSN: | 2304-6740 |