Yishu Bao , Siyuan Ma , Jin Zhu , Zonghao Dai , Qikun Zhou , Xiuqin Yang , Qingfa Zhou , Fulai Yang
{"title":"以 1-四氢萘酮为新型二氢源的 TfOH 催化转移加氢反应","authors":"Yishu Bao , Siyuan Ma , Jin Zhu , Zonghao Dai , Qikun Zhou , Xiuqin Yang , Qingfa Zhou , Fulai Yang","doi":"10.1039/d3gc04699k","DOIUrl":null,"url":null,"abstract":"<div><p>An unprecedented TfOH-catalyzed transfer hydrogenation reaction has been developed using 1-tetralone as a novel dihydrogen source. Various alkenes, as well as triphenylmethyl and diphenylmethyl derivatives, have been successfully employed in this transfer hydrogenation reaction, resulting in the formation of various desired products with good yields. Deuterium labeling experiments show that the α-hydrogen of 1-tetralone donated a proton to the alkene, resulting in the formation of a carbenium ion that subsequently captured a hydride originating from the β-hydrogen of 1-tetralone, thereby facilitating a reduction reaction. This study represents a significant advance as it demonstrates the potential of ketones as novel dihydrogen sources for reduction reactions under metal-free conditions.</p></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":"26 3","pages":"Pages 1356-1362"},"PeriodicalIF":9.3000,"publicationDate":"2024-02-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"TfOH-catalyzed transfer hydrogenation reaction using 1-tetralone as a novel dihydrogen source†\",\"authors\":\"Yishu Bao , Siyuan Ma , Jin Zhu , Zonghao Dai , Qikun Zhou , Xiuqin Yang , Qingfa Zhou , Fulai Yang\",\"doi\":\"10.1039/d3gc04699k\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>An unprecedented TfOH-catalyzed transfer hydrogenation reaction has been developed using 1-tetralone as a novel dihydrogen source. Various alkenes, as well as triphenylmethyl and diphenylmethyl derivatives, have been successfully employed in this transfer hydrogenation reaction, resulting in the formation of various desired products with good yields. Deuterium labeling experiments show that the α-hydrogen of 1-tetralone donated a proton to the alkene, resulting in the formation of a carbenium ion that subsequently captured a hydride originating from the β-hydrogen of 1-tetralone, thereby facilitating a reduction reaction. This study represents a significant advance as it demonstrates the potential of ketones as novel dihydrogen sources for reduction reactions under metal-free conditions.</p></div>\",\"PeriodicalId\":78,\"journal\":{\"name\":\"Green Chemistry\",\"volume\":\"26 3\",\"pages\":\"Pages 1356-1362\"},\"PeriodicalIF\":9.3000,\"publicationDate\":\"2024-02-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Green Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1463926224004722\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Green Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1463926224004722","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
TfOH-catalyzed transfer hydrogenation reaction using 1-tetralone as a novel dihydrogen source†
An unprecedented TfOH-catalyzed transfer hydrogenation reaction has been developed using 1-tetralone as a novel dihydrogen source. Various alkenes, as well as triphenylmethyl and diphenylmethyl derivatives, have been successfully employed in this transfer hydrogenation reaction, resulting in the formation of various desired products with good yields. Deuterium labeling experiments show that the α-hydrogen of 1-tetralone donated a proton to the alkene, resulting in the formation of a carbenium ion that subsequently captured a hydride originating from the β-hydrogen of 1-tetralone, thereby facilitating a reduction reaction. This study represents a significant advance as it demonstrates the potential of ketones as novel dihydrogen sources for reduction reactions under metal-free conditions.
期刊介绍:
Green Chemistry is a journal that provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998), which defines green chemistry as the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry aims to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. The journal welcomes submissions on all aspects of research relating to this endeavor and publishes original and significant cutting-edge research that is likely to be of wide general appeal. For a work to be published, it must present a significant advance in green chemistry, including a comparison with existing methods and a demonstration of advantages over those methods.