{"title":"调谐 Cu2+/TEMPO 催化苯甲醇到苯甲醛的选择性有氧氧化的碱","authors":"Wenjie Yang, Fan Xu, Guojun Shi","doi":"10.1007/s10562-024-04843-3","DOIUrl":null,"url":null,"abstract":"<div><p>Promotional role of basic ligands on the combination of cupric ions and 2,2,6,6-tetramethyl-piperidine-N-noxyl (Cu<sup>2+</sup>/TEMPO) was tried in the previous publications for selective aerobic oxidation of benzyl alcohol but a lack of a detailed investigation encourages us to perform further work. Here, Cu<sup>2+</sup>/TEMPO was used to catalyze selective aerobic oxidation of benzyl alcohol to benzaldehyde in the presence of bases, and triethylamine was found to be the best additive. A conversion of benzyl alcohol of 92.9% and a selectivity to benzaldehyde of 100% was observed in the presence of Cu<sup>2+</sup>/TEMPO/triethylamine. The promotion of triethylamine on Cu<sup>2+</sup>/TEMPO can be related to its capability in electron-donor and deprotonation. The speciation of the ternary catalyst combination was partially observed by the means of high-resolution mass spectroscopy (HRMS) and some key intermediates such as N-hydroxyl-2,2,6,6-tetramethylperidine (TEMPOH) and ethyl-substituted ammonium ions were confirmed. This study might provide some insights into the highly efficient transformation from benzyl alcohol to benzaldehyde and the promotion of bases on this transformation.</p><h3>Graphical Abstract</h3>\n<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":508,"journal":{"name":"Catalysis Letters","volume":"155 1","pages":""},"PeriodicalIF":2.3000,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Bases Tuning Selective Aerobic Oxidation of Benzyl Alcohol to Benzaldehyde Catalyzed by Cu2+/TEMPO\",\"authors\":\"Wenjie Yang, Fan Xu, Guojun Shi\",\"doi\":\"10.1007/s10562-024-04843-3\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Promotional role of basic ligands on the combination of cupric ions and 2,2,6,6-tetramethyl-piperidine-N-noxyl (Cu<sup>2+</sup>/TEMPO) was tried in the previous publications for selective aerobic oxidation of benzyl alcohol but a lack of a detailed investigation encourages us to perform further work. Here, Cu<sup>2+</sup>/TEMPO was used to catalyze selective aerobic oxidation of benzyl alcohol to benzaldehyde in the presence of bases, and triethylamine was found to be the best additive. A conversion of benzyl alcohol of 92.9% and a selectivity to benzaldehyde of 100% was observed in the presence of Cu<sup>2+</sup>/TEMPO/triethylamine. The promotion of triethylamine on Cu<sup>2+</sup>/TEMPO can be related to its capability in electron-donor and deprotonation. The speciation of the ternary catalyst combination was partially observed by the means of high-resolution mass spectroscopy (HRMS) and some key intermediates such as N-hydroxyl-2,2,6,6-tetramethylperidine (TEMPOH) and ethyl-substituted ammonium ions were confirmed. This study might provide some insights into the highly efficient transformation from benzyl alcohol to benzaldehyde and the promotion of bases on this transformation.</p><h3>Graphical Abstract</h3>\\n<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>\",\"PeriodicalId\":508,\"journal\":{\"name\":\"Catalysis Letters\",\"volume\":\"155 1\",\"pages\":\"\"},\"PeriodicalIF\":2.3000,\"publicationDate\":\"2024-11-13\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Catalysis Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s10562-024-04843-3\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Catalysis Letters","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s10562-024-04843-3","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
Bases Tuning Selective Aerobic Oxidation of Benzyl Alcohol to Benzaldehyde Catalyzed by Cu2+/TEMPO
Promotional role of basic ligands on the combination of cupric ions and 2,2,6,6-tetramethyl-piperidine-N-noxyl (Cu2+/TEMPO) was tried in the previous publications for selective aerobic oxidation of benzyl alcohol but a lack of a detailed investigation encourages us to perform further work. Here, Cu2+/TEMPO was used to catalyze selective aerobic oxidation of benzyl alcohol to benzaldehyde in the presence of bases, and triethylamine was found to be the best additive. A conversion of benzyl alcohol of 92.9% and a selectivity to benzaldehyde of 100% was observed in the presence of Cu2+/TEMPO/triethylamine. The promotion of triethylamine on Cu2+/TEMPO can be related to its capability in electron-donor and deprotonation. The speciation of the ternary catalyst combination was partially observed by the means of high-resolution mass spectroscopy (HRMS) and some key intermediates such as N-hydroxyl-2,2,6,6-tetramethylperidine (TEMPOH) and ethyl-substituted ammonium ions were confirmed. This study might provide some insights into the highly efficient transformation from benzyl alcohol to benzaldehyde and the promotion of bases on this transformation.
期刊介绍：
Catalysis Letters aim is the rapid publication of outstanding and high-impact original research articles in catalysis. The scope of the journal covers a broad range of topics in all fields of both applied and theoretical catalysis, including heterogeneous, homogeneous and biocatalysis.
The high-quality original research articles published in Catalysis Letters are subject to rigorous peer review. Accepted papers are published online first and subsequently in print issues. All contributions must include a graphical abstract. Manuscripts should be written in English and the responsibility lies with the authors to ensure that they are grammatically and linguistically correct. Authors for whom English is not the working language are encouraged to consider using a professional language-editing service before submitting their manuscripts.
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