{"title":"Palladium-Catalyzed NHC Ligand-Controlled Regiodivergent Allyl-Fluoroallyl Cross-Couplings","authors":"Yangyang Ma, Boxia Xu, Hua Zhang, Zhiping Li","doi":"10.1039/d4qo01800a","DOIUrl":null,"url":null,"abstract":"The palladium-catalyzed cross-coupling of (E)-2-fluoroallyl carbonates and allylboronates is reported. The regioselectivity is susceptive to the steric requirements of the NHC ligand, with small IMes favoring the linear fluorinated 1,5-dienes, while the IPrBIDEA featuring sterically-congested character benefits the branched products. Control experiments revealed that either 2-fluoroallyl carbonates or gem-F2CPs could undergo allylation with excellent regioselectivity, yet the former behaved with some lower branched reactivity.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"253 1","pages":""},"PeriodicalIF":4.6000,"publicationDate":"2024-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4qo01800a","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
The palladium-catalyzed cross-coupling of (E)-2-fluoroallyl carbonates and allylboronates is reported. The regioselectivity is susceptive to the steric requirements of the NHC ligand, with small IMes favoring the linear fluorinated 1,5-dienes, while the IPrBIDEA featuring sterically-congested character benefits the branched products. Control experiments revealed that either 2-fluoroallyl carbonates or gem-F2CPs could undergo allylation with excellent regioselectivity, yet the former behaved with some lower branched reactivity.
期刊介绍：
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
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