{"title":"Visible-Light-Induced Palladium-Mediated Allylic C–H Alkylation Reaction","authors":"Kun-Yu Huang, , , Wei-Dong Lu, , , Xiao-Qing Chen, , , Kai Chen, , , Yu Zheng*, , and , Hua Yang*, ","doi":"10.1021/acs.orglett.5c03515","DOIUrl":null,"url":null,"abstract":"<p >Direct C–H alkylation is one of the most important C–C bond formation events and is crucial to the efficient assembly of functionalized carbon skeletons in synthetic chemistry. We report herein a photoinduced palladium-catalyzed strategy for the direct alkylation of allylic C–H bonds. The success of this transformation relies on the use of 2-bromo-1,3-dimethylbenzene as a hydrogen atom transfer (HAT) mediator, in combination with a carbon nucleophile, facilitated by a palladium catalyst activated by blue light. Unlike classical Pd(II/0) pathways, this approach leverages the versatile reactivity of Pd(0/I/II) species through visible-light excitation, establishing a robust foundation for the feasibility of this synthetic methodology.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 39","pages":"11083–11088"},"PeriodicalIF":5.0000,"publicationDate":"2025-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.orglett.5c03515","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Direct C–H alkylation is one of the most important C–C bond formation events and is crucial to the efficient assembly of functionalized carbon skeletons in synthetic chemistry. We report herein a photoinduced palladium-catalyzed strategy for the direct alkylation of allylic C–H bonds. The success of this transformation relies on the use of 2-bromo-1,3-dimethylbenzene as a hydrogen atom transfer (HAT) mediator, in combination with a carbon nucleophile, facilitated by a palladium catalyst activated by blue light. Unlike classical Pd(II/0) pathways, this approach leverages the versatile reactivity of Pd(0/I/II) species through visible-light excitation, establishing a robust foundation for the feasibility of this synthetic methodology.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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