Panyi Huang , Yan Xu , Haijing Song , Jiayin Wang , Jiayang Wang , Jianjun Li , Bin Sun , Can Jin
{"title":"Selective C(sp3)–H bond aerobic oxidation enabled by a π-conjugated small molecule-oxygen charge transfer state†","authors":"Panyi Huang , Yan Xu , Haijing Song , Jiayin Wang , Jiayang Wang , Jianjun Li , Bin Sun , Can Jin","doi":"10.1039/d4gc02010c","DOIUrl":null,"url":null,"abstract":"<div><p>Due to the high oxidation potential of arenes and alkenes, previous methods of benzylic and allylic C–H oxidation necessitated the use of strong oxidizing agents, metal catalysts, or free radical initiators (such as photocatalysts or hydrogen atom transfer reagents) to be effective. Herein, we employ oxygen to generate a triple-spin charge transfer state with π-conjugated compounds effectively accessing the triplet excited states of arenes, followed by energy transfer to form singlet oxygen facilitating C–H bond oxidation. Distinct from previous oxidations, it is the first time that a series of natural products and drug molecules (27 examples) are selectively oxidized without any catalysts or additives. The transformation can be implemented under sunlight to produce valuable unsaturated (aromatic) ketones and only water as waste, which meets every one of the 12 principles of green chemistry.</p></div>","PeriodicalId":78,"journal":{"name":"Green Chemistry","volume":null,"pages":null},"PeriodicalIF":9.3000,"publicationDate":"2024-08-12","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/S1463926224006885","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Due to the high oxidation potential of arenes and alkenes, previous methods of benzylic and allylic C–H oxidation necessitated the use of strong oxidizing agents, metal catalysts, or free radical initiators (such as photocatalysts or hydrogen atom transfer reagents) to be effective. Herein, we employ oxygen to generate a triple-spin charge transfer state with π-conjugated compounds effectively accessing the triplet excited states of arenes, followed by energy transfer to form singlet oxygen facilitating C–H bond oxidation. Distinct from previous oxidations, it is the first time that a series of natural products and drug molecules (27 examples) are selectively oxidized without any catalysts or additives. The transformation can be implemented under sunlight to produce valuable unsaturated (aromatic) ketones and only water as waste, which meets every one of the 12 principles of green chemistry.
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.
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号
