简单的1,3-二烯直接催化合成功能化二烯:金属催化剂取代1,3-丁二烯、异戊二烯和2,3-二甲基-1,3-丁二烯的研究进展

IF 4.8 2区 化学 Q2 CHEMISTRY, PHYSICAL
Yukio Hamamoto, Yasushi Obora
{"title":"简单的1,3-二烯直接催化合成功能化二烯:金属催化剂取代1,3-丁二烯、异戊二烯和2,3-二甲基-1,3-丁二烯的研究进展","authors":"Yukio Hamamoto,&nbsp;Yasushi Obora","doi":"10.1016/j.apcata.2025.120572","DOIUrl":null,"url":null,"abstract":"<div><div>Conjugated diene structures are important as feedstocks for many organic reactions. Therefore, development of efficient syntheses of conjugated diene compounds is desirable. This review introduces selective functionalizing reactions to 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene with various metal catalysts, ligands, and types of reactions. To overcome difficulties of controlling reactions, Heck reactions with Pd or Ni catalysts and metathesis cross couplings with Grubbs catalysts are mainly used. Focused on ligands, phosphines, 1,5-cyclooctadiene, imidazoline derivatives are frequently used. As a plausible mechanism, formation of π-allyl complexes is concerned as an initial step, especially when palladium is used. Then, as an intermediate, η<sup>2</sup>-π-allyl metal are formed. At last, reductive elimination undergoes and the desired compounds are obtained. Reaction mechanisms are concerned by labelling experiment or isolation of intermediates in most examples. In addition, in most reactions, results of substrate scope that not only 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene are used are depicted. Besides, several applications of functionalized dienes are introduced. As a result, synthesized dienes are converted into (hetero)cyclic compounds, polyenes, enyl ketones. Overall, diene is considered a useful starting material for addition reactions such as polymerization, telomerization, and annulation and functionalizing dienes is expected to facilitate the efficient synthesis of organic compounds with complex structures by upgrading simple 1,3-diene.</div></div>","PeriodicalId":243,"journal":{"name":"Applied Catalysis A: General","volume":"708 ","pages":"Article 120572"},"PeriodicalIF":4.8000,"publicationDate":"2025-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Direct catalytic synthesis of functionalized dienes from simple 1,3-dienes: A review on substitution of 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene with metal catalysts\",\"authors\":\"Yukio Hamamoto,&nbsp;Yasushi Obora\",\"doi\":\"10.1016/j.apcata.2025.120572\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Conjugated diene structures are important as feedstocks for many organic reactions. Therefore, development of efficient syntheses of conjugated diene compounds is desirable. This review introduces selective functionalizing reactions to 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene with various metal catalysts, ligands, and types of reactions. To overcome difficulties of controlling reactions, Heck reactions with Pd or Ni catalysts and metathesis cross couplings with Grubbs catalysts are mainly used. Focused on ligands, phosphines, 1,5-cyclooctadiene, imidazoline derivatives are frequently used. As a plausible mechanism, formation of π-allyl complexes is concerned as an initial step, especially when palladium is used. Then, as an intermediate, η<sup>2</sup>-π-allyl metal are formed. At last, reductive elimination undergoes and the desired compounds are obtained. Reaction mechanisms are concerned by labelling experiment or isolation of intermediates in most examples. In addition, in most reactions, results of substrate scope that not only 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene are used are depicted. Besides, several applications of functionalized dienes are introduced. As a result, synthesized dienes are converted into (hetero)cyclic compounds, polyenes, enyl ketones. Overall, diene is considered a useful starting material for addition reactions such as polymerization, telomerization, and annulation and functionalizing dienes is expected to facilitate the efficient synthesis of organic compounds with complex structures by upgrading simple 1,3-diene.</div></div>\",\"PeriodicalId\":243,\"journal\":{\"name\":\"Applied Catalysis A: General\",\"volume\":\"708 \",\"pages\":\"Article 120572\"},\"PeriodicalIF\":4.8000,\"publicationDate\":\"2025-09-15\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Applied Catalysis A: General\",\"FirstCategoryId\":\"1\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0926860X25004740\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, PHYSICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Applied Catalysis A: General","FirstCategoryId":"1","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0926860X25004740","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0

摘要

共轭二烯结构是许多有机反应的重要原料。因此,开发高效合成共轭二烯类化合物是很有必要的。本文综述了不同金属催化剂、配体和反应类型对1,3-丁二烯、异戊二烯、2,3-二甲基-1,3-丁二烯的选择性功能化反应。为了克服控制反应的困难,主要采用与Pd或Ni催化剂的Heck反应和与Grubbs催化剂的复分解交叉偶联。在配体方面,膦、1,5-环二烯、咪唑啉衍生物是常用的配体。作为一个合理的机制,π-烯丙基配合物的形成被认为是第一步,特别是当钯被使用时。然后,作为中间产物,形成η - 2 π-烯丙基金属。最后进行还原消除,得到所需的化合物。在大多数情况下,反应机理与标记实验或中间产物的分离有关。此外,在大多数反应中,底物范围的结果不仅描述了使用1,3-丁二烯,异戊二烯,2,3-二甲基-1,3-丁二烯。此外,还介绍了功能化二烯的几种应用。结果,合成的二烯被转化为(杂)环化合物、多烯、烯基酮。总的来说,二烯被认为是一种有用的加成反应的起始材料,如聚合、端粒化和环化,而功能化二烯有望通过升级简单的1,3-二烯来促进具有复杂结构的有机化合物的高效合成。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Direct catalytic synthesis of functionalized dienes from simple 1,3-dienes: A review on substitution of 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene with metal catalysts
Conjugated diene structures are important as feedstocks for many organic reactions. Therefore, development of efficient syntheses of conjugated diene compounds is desirable. This review introduces selective functionalizing reactions to 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene with various metal catalysts, ligands, and types of reactions. To overcome difficulties of controlling reactions, Heck reactions with Pd or Ni catalysts and metathesis cross couplings with Grubbs catalysts are mainly used. Focused on ligands, phosphines, 1,5-cyclooctadiene, imidazoline derivatives are frequently used. As a plausible mechanism, formation of π-allyl complexes is concerned as an initial step, especially when palladium is used. Then, as an intermediate, η2-π-allyl metal are formed. At last, reductive elimination undergoes and the desired compounds are obtained. Reaction mechanisms are concerned by labelling experiment or isolation of intermediates in most examples. In addition, in most reactions, results of substrate scope that not only 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene are used are depicted. Besides, several applications of functionalized dienes are introduced. As a result, synthesized dienes are converted into (hetero)cyclic compounds, polyenes, enyl ketones. Overall, diene is considered a useful starting material for addition reactions such as polymerization, telomerization, and annulation and functionalizing dienes is expected to facilitate the efficient synthesis of organic compounds with complex structures by upgrading simple 1,3-diene.
求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
Applied Catalysis A: General
Applied Catalysis A: General 化学-环境科学
CiteScore
9.00
自引率
5.50%
发文量
415
审稿时长
24 days
期刊介绍: Applied Catalysis A: General publishes original papers on all aspects of catalysis of basic and practical interest to chemical scientists in both industrial and academic fields, with an emphasis onnew understanding of catalysts and catalytic reactions, new catalytic materials, new techniques, and new processes, especially those that have potential practical implications. Papers that report results of a thorough study or optimization of systems or processes that are well understood, widely studied, or minor variations of known ones are discouraged. Authors should include statements in a separate section "Justification for Publication" of how the manuscript fits the scope of the journal in the cover letter to the editors. Submissions without such justification will be rejected without review.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术官方微信