{"title":"钯(II)催化的 1,3-杂芳基丙炔酰氧基化原炔电介质","authors":"Shenghan Teng, Peiyao Liang, Lin Hu, Siyi Chen, Shoulei Wang, Wei Huang","doi":"10.1039/d4qo00869c","DOIUrl":null,"url":null,"abstract":"We report a 1,3-heteroaryl acyloxylation of 3-substituted propargylic esters with readily available heteroarenes including indoles, pyrroles, furans and thiophenes under palladium catalysis. The heteroaryl-functionalized Z-enol ester products are obtained in a single step with complete levels of γ-regioselectivity and anti-hydroacetoxylation stereocontrol. The use of palladium-tri(2-furyl)phosphine complex in polyfluorinated alcoholic solvents has proven to be crucial to the reactivity of the desired pathway based on control experiments. High atom economy, mild conditions (30 °C) and broad functional group tolerance make this protocol attractive. Finally, the synthetic utility of this method is demonstrated by gram-scale synthesis and downstream derivatizations of the product.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Palladium(II)-Catalyzed 1,3-Heteroaryl Acyloxylation of Propargylic Electrophiles\",\"authors\":\"Shenghan Teng, Peiyao Liang, Lin Hu, Siyi Chen, Shoulei Wang, Wei Huang\",\"doi\":\"10.1039/d4qo00869c\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"We report a 1,3-heteroaryl acyloxylation of 3-substituted propargylic esters with readily available heteroarenes including indoles, pyrroles, furans and thiophenes under palladium catalysis. The heteroaryl-functionalized Z-enol ester products are obtained in a single step with complete levels of γ-regioselectivity and anti-hydroacetoxylation stereocontrol. The use of palladium-tri(2-furyl)phosphine complex in polyfluorinated alcoholic solvents has proven to be crucial to the reactivity of the desired pathway based on control experiments. High atom economy, mild conditions (30 °C) and broad functional group tolerance make this protocol attractive. Finally, the synthetic utility of this method is demonstrated by gram-scale synthesis and downstream derivatizations of the product.\",\"PeriodicalId\":97,\"journal\":{\"name\":\"Organic Chemistry Frontiers\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.6000,\"publicationDate\":\"2024-06-27\",\"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/d4qo00869c\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4qo00869c","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Palladium(II)-Catalyzed 1,3-Heteroaryl Acyloxylation of Propargylic Electrophiles
We report a 1,3-heteroaryl acyloxylation of 3-substituted propargylic esters with readily available heteroarenes including indoles, pyrroles, furans and thiophenes under palladium catalysis. The heteroaryl-functionalized Z-enol ester products are obtained in a single step with complete levels of γ-regioselectivity and anti-hydroacetoxylation stereocontrol. The use of palladium-tri(2-furyl)phosphine complex in polyfluorinated alcoholic solvents has proven to be crucial to the reactivity of the desired pathway based on control experiments. High atom economy, mild conditions (30 °C) and broad functional group tolerance make this protocol attractive. Finally, the synthetic utility of this method is demonstrated by gram-scale synthesis and downstream derivatizations of the product.
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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