{"title":"(E)-β,γ-不饱和羧酸的底物定向区域选择性烯官能化。","authors":"Chi-Hao Chang, Chao-Ting Yen, Théo P Goncalves, Yu-Sheng Lin, Yu-Chun Wang, R Sidick Basha, Bo-Yan Chen, Cheng-Hao Fu, Liang-Wei Chen, Meng-Li Jhou, Kuo-Wei Huang, Chih-Ming Chou","doi":"10.1039/d4cc03581j","DOIUrl":null,"url":null,"abstract":"<p><p>A carboxylate-directed regioselective Heck-type alkenylation and alkenylative lactonization of (<i>E</i>)-β,γ-unsaturated carboxylic acids by simply substrate control is reported. (<i>E</i>)- and (<i>Z</i>)-alkenyl bromides reacted to give energetically more favorable palladacyles, allowing access to fully stereocontrolled conjugated 1,3-dienes and alkenyled γ-lactones. Mechanistic studies suggest that excellent regioselectivity may be strongly influenced by the steric factors of reactants involved in the palladacycle intermediates.</p>","PeriodicalId":67,"journal":{"name":"Chemical Communications","volume":null,"pages":null},"PeriodicalIF":4.3000,"publicationDate":"2024-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Substrate-directed regioselective alkene functionalizations of (<i>E</i>)-β,γ-unsaturated carboxylic acids.\",\"authors\":\"Chi-Hao Chang, Chao-Ting Yen, Théo P Goncalves, Yu-Sheng Lin, Yu-Chun Wang, R Sidick Basha, Bo-Yan Chen, Cheng-Hao Fu, Liang-Wei Chen, Meng-Li Jhou, Kuo-Wei Huang, Chih-Ming Chou\",\"doi\":\"10.1039/d4cc03581j\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>A carboxylate-directed regioselective Heck-type alkenylation and alkenylative lactonization of (<i>E</i>)-β,γ-unsaturated carboxylic acids by simply substrate control is reported. (<i>E</i>)- and (<i>Z</i>)-alkenyl bromides reacted to give energetically more favorable palladacyles, allowing access to fully stereocontrolled conjugated 1,3-dienes and alkenyled γ-lactones. Mechanistic studies suggest that excellent regioselectivity may be strongly influenced by the steric factors of reactants involved in the palladacycle intermediates.</p>\",\"PeriodicalId\":67,\"journal\":{\"name\":\"Chemical Communications\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.3000,\"publicationDate\":\"2024-10-03\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemical Communications\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d4cc03581j\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical Communications","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4cc03581j","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Substrate-directed regioselective alkene functionalizations of (E)-β,γ-unsaturated carboxylic acids.
A carboxylate-directed regioselective Heck-type alkenylation and alkenylative lactonization of (E)-β,γ-unsaturated carboxylic acids by simply substrate control is reported. (E)- and (Z)-alkenyl bromides reacted to give energetically more favorable palladacyles, allowing access to fully stereocontrolled conjugated 1,3-dienes and alkenyled γ-lactones. Mechanistic studies suggest that excellent regioselectivity may be strongly influenced by the steric factors of reactants involved in the palladacycle intermediates.
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