Aabid A. Wani , Shivkanya Madhavrao Bhujbal , Deekey Sherpa , Deepika Kathuria , Sumit S. Chourasiya , Subash C. Sahoo , Prasad V. Bharatam
{"title":"一种含有 1,1-二氨基嗪的 NNN Pd(II) 夹板配合物:无受体脱氢偶联反应的多功能催化剂。","authors":"Aabid A. Wani , Shivkanya Madhavrao Bhujbal , Deekey Sherpa , Deepika Kathuria , Sumit S. Chourasiya , Subash C. Sahoo , Prasad V. Bharatam","doi":"10.1039/d4ob01576b","DOIUrl":null,"url":null,"abstract":"<div><div>An azine-based, non-palindromic, neutral NNN-pincer ligand was synthesised in a single step with an yield of 85%. The palladation of the ligand, using Pd(OAc)<sub>2</sub>, was performed in acetonitrile at room temperature to obtain the pincer complex in 88% yield through a simple, cost-effective, and straightforward synthetic procedure. The structure of the complex was confirmed by <sup>1</sup>H NMR, <sup>13</sup>C NMR, FT-IR, and mass spectrometry. The variable temperature NMR spectra revealed the stability of the complex even at higher temperatures, a characteristic feature of pincer complexes. The generated complex proved to be a versatile catalyst for Acceptorless Dehydrogenative Coupling (ADC) to synthesize <em>N</em>-heterocycles: (i) 1,2-disubstituted benzimidazoles, (ii) 2-phenylquinolines, (iii) 2-phenylquinoxalines and (iv) 2-phenylquinazolinones. Since the side products of the reactions are H<sub>2</sub>O and H<sub>2</sub> gas, the catalysis can be considered as a green catalytic process. Quantum chemical calculations indicated the participation of a possible nitrene–imide conversion process during the Metal–Ligand Cooperation (MLC) in ADC reactions.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 2","pages":"Pages 343-351"},"PeriodicalIF":2.9000,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"An NNN Pd(ii) pincer complex with 1,1-diaminoazine: a versatile catalyst for acceptorless dehydrogenative coupling reactions†\",\"authors\":\"Aabid A. Wani , Shivkanya Madhavrao Bhujbal , Deekey Sherpa , Deepika Kathuria , Sumit S. Chourasiya , Subash C. Sahoo , Prasad V. Bharatam\",\"doi\":\"10.1039/d4ob01576b\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>An azine-based, non-palindromic, neutral NNN-pincer ligand was synthesised in a single step with an yield of 85%. The palladation of the ligand, using Pd(OAc)<sub>2</sub>, was performed in acetonitrile at room temperature to obtain the pincer complex in 88% yield through a simple, cost-effective, and straightforward synthetic procedure. The structure of the complex was confirmed by <sup>1</sup>H NMR, <sup>13</sup>C NMR, FT-IR, and mass spectrometry. The variable temperature NMR spectra revealed the stability of the complex even at higher temperatures, a characteristic feature of pincer complexes. The generated complex proved to be a versatile catalyst for Acceptorless Dehydrogenative Coupling (ADC) to synthesize <em>N</em>-heterocycles: (i) 1,2-disubstituted benzimidazoles, (ii) 2-phenylquinolines, (iii) 2-phenylquinoxalines and (iv) 2-phenylquinazolinones. Since the side products of the reactions are H<sub>2</sub>O and H<sub>2</sub> gas, the catalysis can be considered as a green catalytic process. Quantum chemical calculations indicated the participation of a possible nitrene–imide conversion process during the Metal–Ligand Cooperation (MLC) in ADC reactions.</div></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":\"23 2\",\"pages\":\"Pages 343-351\"},\"PeriodicalIF\":2.9000,\"publicationDate\":\"2024-11-06\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1477052024010140\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052024010140","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
An NNN Pd(ii) pincer complex with 1,1-diaminoazine: a versatile catalyst for acceptorless dehydrogenative coupling reactions†
An azine-based, non-palindromic, neutral NNN-pincer ligand was synthesised in a single step with an yield of 85%. The palladation of the ligand, using Pd(OAc)2, was performed in acetonitrile at room temperature to obtain the pincer complex in 88% yield through a simple, cost-effective, and straightforward synthetic procedure. The structure of the complex was confirmed by 1H NMR, 13C NMR, FT-IR, and mass spectrometry. The variable temperature NMR spectra revealed the stability of the complex even at higher temperatures, a characteristic feature of pincer complexes. The generated complex proved to be a versatile catalyst for Acceptorless Dehydrogenative Coupling (ADC) to synthesize N-heterocycles: (i) 1,2-disubstituted benzimidazoles, (ii) 2-phenylquinolines, (iii) 2-phenylquinoxalines and (iv) 2-phenylquinazolinones. Since the side products of the reactions are H2O and H2 gas, the catalysis can be considered as a green catalytic process. Quantum chemical calculations indicated the participation of a possible nitrene–imide conversion process during the Metal–Ligand Cooperation (MLC) in ADC reactions.
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.