{"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":9501,"journal":{"name":"Bulletin of the Chemical Society of Ethiopia","volume":null,"pages":null},"PeriodicalIF":1.3000,"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\":9501,\"journal\":{\"name\":\"Bulletin of the Chemical Society of Ethiopia\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.3000,\"publicationDate\":\"2024-07-12\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Bulletin of the Chemical Society of Ethiopia\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.4314/bcse.v38i5.16\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Bulletin of the Chemical Society of Ethiopia","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.4314/bcse.v38i5.16","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","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：
The Bulletin of the Chemical Society of Ethiopia (BCSE) is a triannual publication of the Chemical Society of Ethiopia. The BCSE is an open access and peer reviewed journal. The BCSE invites contributions in any field of basic and applied chemistry.
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