{"title":"利用 Ni(II) 介导的 Suzuki-Miyaura 反应合成 1,3-二烯","authors":"Yassir S. Al-Jawaheri, Nameer S. Ezzat","doi":"10.4314/bcse.v38i5.16","DOIUrl":null,"url":null,"abstract":"Synthesis of the 1,3-dienes from arylboronic acids with propargyl alcohols using a Ni(II) precatalysts is presented. Through detailed reaction screening NiCl2(PCy3)2 has been identified as the optimal catalyst for this transformation. The reaction is thought to proceed through a Ni(II) allenyl complex, which undergoes a base free Suzuki-Miyaura cross-coupling through arylboronic acids, with the resultant aryl allene rearranging to its 1,3-diene. Application of these optimized reaction conditions then provides several dienes in reasonable to good, isolated yields. \nKEY WORDS: Suzuki-Miyaura, NiCl2(PCy3)2, 1,3-Dienes, Allenyl, Base free \nBull. Chem. Soc. Ethiop. 2024, 38(5), 1405-1412. \nDOI: https://dx.doi.org/10.4314/bcse.v38i5.16 ","PeriodicalId":1,"journal":{"name":"Accounts of Chemical Research","volume":"7 11","pages":""},"PeriodicalIF":17.7000,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"A synthesis of 1,3-dienes using a Ni(II) mediated Suzuki-Miyaura reaction\",\"authors\":\"Yassir S. Al-Jawaheri, Nameer S. Ezzat\",\"doi\":\"10.4314/bcse.v38i5.16\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Synthesis of the 1,3-dienes from arylboronic acids with propargyl alcohols using a Ni(II) precatalysts is presented. Through detailed reaction screening NiCl2(PCy3)2 has been identified as the optimal catalyst for this transformation. The reaction is thought to proceed through a Ni(II) allenyl complex, which undergoes a base free Suzuki-Miyaura cross-coupling through arylboronic acids, with the resultant aryl allene rearranging to its 1,3-diene. Application of these optimized reaction conditions then provides several dienes in reasonable to good, isolated yields. \\nKEY WORDS: Suzuki-Miyaura, NiCl2(PCy3)2, 1,3-Dienes, Allenyl, Base free \\nBull. Chem. Soc. Ethiop. 2024, 38(5), 1405-1412. \\nDOI: https://dx.doi.org/10.4314/bcse.v38i5.16 \",\"PeriodicalId\":1,\"journal\":{\"name\":\"Accounts of Chemical Research\",\"volume\":\"7 11\",\"pages\":\"\"},\"PeriodicalIF\":17.7000,\"publicationDate\":\"2024-07-12\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Accounts of Chemical Research\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.4314/bcse.v38i5.16\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Accounts of Chemical Research","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.4314/bcse.v38i5.16","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
A synthesis of 1,3-dienes using a Ni(II) mediated Suzuki-Miyaura reaction
Synthesis of the 1,3-dienes from arylboronic acids with propargyl alcohols using a Ni(II) precatalysts is presented. Through detailed reaction screening NiCl2(PCy3)2 has been identified as the optimal catalyst for this transformation. The reaction is thought to proceed through a Ni(II) allenyl complex, which undergoes a base free Suzuki-Miyaura cross-coupling through arylboronic acids, with the resultant aryl allene rearranging to its 1,3-diene. Application of these optimized reaction conditions then provides several dienes in reasonable to good, isolated yields.
KEY WORDS: Suzuki-Miyaura, NiCl2(PCy3)2, 1,3-Dienes, Allenyl, Base free
Bull. Chem. Soc. Ethiop. 2024, 38(5), 1405-1412.
DOI: https://dx.doi.org/10.4314/bcse.v38i5.16
期刊介绍：
Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance.
Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.
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