中国科学院上海有机化学研究所机构知识库
Advanced  
SIOC OpenIR  > 金属有机化学国家重点实验室  > 期刊论文
学科主题: 金属有机化学
题名: Palladium-Catalyzed Cyclization Reactions of Allenes in the Presence of Unsaturated Carbon-Carbon Bonds
其他题名: 钯催化的在不饱和碳碳键存在下的联烯环化反应
作者: Ye JT(叶俊涛)1; Ma SM(麻生明)1
通讯作者: 麻生明
刊名: Accounts Chem. Res.
发表日期: 2014
DOI: 10.1021/ar4002069
卷: 47, 期:4, 页:989-1000
收录类别: SCI
英文摘要: CONSPECTUS: Modern synthetic chemists have looked for rapid and efficient ways to construct complex molecules while minimizing synthetic manipulation and maximizing atom-economy. Over the last few decades, researchers have made considerable progress toward these goals by taking full advantage of transition metal catalysis and the diverse reactivities of allenes, functional groups which include two cumulative carbon carbon double bonds. This Account describes our efforts toward the development of Pd-catalyzed cyclization reactions of allenes in the presence of compounds that contain unsaturated carbon carbon bonds such as alkenyl halides, simple alkenes, allenes, electron-deficient alkynes, or propargylic carbonates. First, we discuss the coupling-cyclization reactions of allenes bearing a nucleophilic functionality in the presence of alkenyl halides, simple alkenes, functionalized and nonfunctionalized allenes, or electron-deficient alkynes. These processes generally involve a Pd(II)-catalyzed sequence: cyclic nucleopalladation, insertion or nucleopalladation, and beta-elimination, reductive elimination, cyclic allylation or protonation. We then focus on Pd(0)-catalyzed cyclization reactions of allenes in the presence of propargylic carbonates. In these transformations, oxidative addition of propargylic carbonates with Pd(0) affords allenylpalladium-(II) species, which then react with allenes via insertion or nucleopalladation. These transformations provide easy access to a variety of synthetically versatile monocyclic, dumbbell-type bicyclic, and fused multicyclic compounds. We have also prepared a series of highly enantioenriched products using an axial-to-central chirality transfer strategy. A range of allenes are now readily available, including optically active ones with central and/or axial chirality. Expansion of these reactions to include other types of functionalized allenes, such as allenyl thiols, allenyl hydroxyl amines, and other structures with differing steric and electronic character, could allow access to cyclic skeletons that previously were difficult to prepare. We anticipate that other studies will continue to explore this promising area of synthetic organic chemistry.
语种: 英语
相关网址: 查看原文
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/39055
Appears in Collections:金属有机化学国家重点实验室_期刊论文

Files in This Item: Download All
File Name/ File Size Content Type Version Access License
2014185.pdf(2196KB)期刊论文作者接受稿开放获取View Download

作者单位: 1.中科院上海有机化学研究所
2.浙江大学

Recommended Citation:
Ye JT,Ma SM. Palladium-Catalyzed Cyclization Reactions of Allenes in the Presence of Unsaturated Carbon-Carbon Bonds[J]. Accounts Chem. Res.,2014,47(4):989-1000.
Service
Recommend this item
Sava as my favorate item
Show this item's statistics
Export Endnote File
Google Scholar
Similar articles in Google Scholar
[叶俊涛]'s Articles
[麻生明]'s Articles
CSDL cross search
Similar articles in CSDL Cross Search
[叶俊涛]‘s Articles
[麻生明]‘s Articles
Related Copyright Policies
Null
Social Bookmarking
Add to CiteULike Add to Connotea Add to Del.icio.us Add to Digg Add to Reddit
文件名: 2014185.pdf
格式: Adobe PDF
此文件暂不支持浏览
所有评论 (0)
暂无评论
 
评注功能仅针对注册用户开放,请您登录
您对该条目有什么异议,请填写以下表单,管理员会尽快联系您。
内 容:
Email:  *
单位:
验证码:   刷新
您在IR的使用过程中有什么好的想法或者建议可以反馈给我们。
标 题:
 *
内 容:
Email:  *
验证码:   刷新

Items in IR are protected by copyright, with all rights reserved, unless otherwise indicated.

 

 

Valid XHTML 1.0!
Powered by CSpace