Yan Li, Xinyuan He, Pengfei Song, Prof. Dr. Hanlin Huang, Prof. Dr. Zhigang Chai
{"title":"C(sp3) -H在流动中通过非均相光催化形成C(sp3) -C (sp3)键的醇活化","authors":"Yan Li, Xinyuan He, Pengfei Song, Prof. Dr. Hanlin Huang, Prof. Dr. Zhigang Chai","doi":"10.1002/cctc.202500894","DOIUrl":null,"url":null,"abstract":"<p>C(sp<sup>3</sup>)‒H activation of alcohols enables creating new C─C bond while keeping hydroxyl group in a step and atom economic manner. Here, we disclose a protocol of coupling alcohols with alkenes for C(sp<sup>3</sup>)‒C(sp<sup>3</sup>) bond formation via heterogeneous photocatalysis in flow. This protocol functions well with a broad scope of alcohols (primary and secondary alcohols) and alkenes with moderate to good yields. The heterogeneous photocatalysis in flow enables current methodology to be conducted even on gram scale, exhibiting great potential for industrial applications. Cleavage of α-C(sp<sup>3</sup>)‒H of alcohol is induced by S<sup>•</sup> species on the surface of ZnIn<sub>2</sub>S<sub>4</sub> via hydrogen atom transfer (HAT), and this step was found to be involved in the rate-determining step.</p>","PeriodicalId":141,"journal":{"name":"ChemCatChem","volume":"17 17","pages":""},"PeriodicalIF":3.9000,"publicationDate":"2025-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"C(sp3)‒H Activation of Alcohol for C(sp3)‒C(sp3) Bond Formation via Heterogeneous Photocatalysis in Flow\",\"authors\":\"Yan Li, Xinyuan He, Pengfei Song, Prof. Dr. Hanlin Huang, Prof. Dr. Zhigang Chai\",\"doi\":\"10.1002/cctc.202500894\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>C(sp<sup>3</sup>)‒H activation of alcohols enables creating new C─C bond while keeping hydroxyl group in a step and atom economic manner. Here, we disclose a protocol of coupling alcohols with alkenes for C(sp<sup>3</sup>)‒C(sp<sup>3</sup>) bond formation via heterogeneous photocatalysis in flow. This protocol functions well with a broad scope of alcohols (primary and secondary alcohols) and alkenes with moderate to good yields. The heterogeneous photocatalysis in flow enables current methodology to be conducted even on gram scale, exhibiting great potential for industrial applications. Cleavage of α-C(sp<sup>3</sup>)‒H of alcohol is induced by S<sup>•</sup> species on the surface of ZnIn<sub>2</sub>S<sub>4</sub> via hydrogen atom transfer (HAT), and this step was found to be involved in the rate-determining step.</p>\",\"PeriodicalId\":141,\"journal\":{\"name\":\"ChemCatChem\",\"volume\":\"17 17\",\"pages\":\"\"},\"PeriodicalIF\":3.9000,\"publicationDate\":\"2025-07-03\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ChemCatChem\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cctc.202500894\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ChemCatChem","FirstCategoryId":"92","ListUrlMain":"https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cctc.202500894","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
C(sp3)‒H Activation of Alcohol for C(sp3)‒C(sp3) Bond Formation via Heterogeneous Photocatalysis in Flow
C(sp3)‒H activation of alcohols enables creating new C─C bond while keeping hydroxyl group in a step and atom economic manner. Here, we disclose a protocol of coupling alcohols with alkenes for C(sp3)‒C(sp3) bond formation via heterogeneous photocatalysis in flow. This protocol functions well with a broad scope of alcohols (primary and secondary alcohols) and alkenes with moderate to good yields. The heterogeneous photocatalysis in flow enables current methodology to be conducted even on gram scale, exhibiting great potential for industrial applications. Cleavage of α-C(sp3)‒H of alcohol is induced by S• species on the surface of ZnIn2S4 via hydrogen atom transfer (HAT), and this step was found to be involved in the rate-determining step.
期刊介绍:
With an impact factor of 4.495 (2018), ChemCatChem is one of the premier journals in the field of catalysis. The journal provides primary research papers and critical secondary information on heterogeneous, homogeneous and bio- and nanocatalysis. The journal is well placed to strengthen cross-communication within between these communities. Its authors and readers come from academia, the chemical industry, and government laboratories across the world. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies, and is supported by the German Catalysis Society.