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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2025-01-01
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| author | Satoshi Sakaguchi Takashi Higashino Yudai Tasaki Ryo Ichihara Tatsuo Yajima |
| author_facet | Satoshi Sakaguchi Takashi Higashino Yudai Tasaki Ryo Ichihara Tatsuo Yajima |
| author_sort | Satoshi Sakaguchi |
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| description | 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. |
| format | Article |
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| institution | Kabale University |
| issn | 2304-6740 |
| language | English |
| publishDate | 2025-01-01 |
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| spelling | doaj-art-2fa6aae9bdfe411fb52db27a0cd055ab2025-01-24T13:35:30ZengMDPI AGInorganics2304-67402025-01-011311810.3390/inorganics13010018Reactions 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 LigandSatoshi Sakaguchi0Takashi Higashino1Yudai Tasaki2Ryo Ichihara3Tatsuo Yajima4Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University, Suita, Osaka 564-8680, JapanDepartment of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University, Suita, Osaka 564-8680, JapanDepartment of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University, Suita, Osaka 564-8680, JapanDepartment of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University, Suita, Osaka 564-8680, JapanDepartment of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University, Suita, Osaka 564-8680, JapanThis 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.https://www.mdpi.com/2304-6740/13/1/18<i>N</i>-heterocyclic carbeneNHC–silver complexesNHC–gold complexhydrolysisformamide |
| spellingShingle | Satoshi Sakaguchi Takashi Higashino Yudai Tasaki Ryo Ichihara Tatsuo Yajima 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 Inorganics <i>N</i>-heterocyclic carbene NHC–silver complexes NHC–gold complex hydrolysis formamide |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | <i>N</i>-heterocyclic carbene NHC–silver complexes NHC–gold complex hydrolysis formamide |
| url | https://www.mdpi.com/2304-6740/13/1/18 |
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