Catalytic Properties of Sterically Shielded Carbene Complexes of Palladium in C–C and C–N Coupling Reactions of Haloarenes

IF 0.7 4区 化学 Q4 CHEMISTRY, MULTIDISCIPLINARY Theoretical and Experimental Chemistry Pub Date : 2024-06-03 DOI:10.1007/s11237-024-09801-z
V. Sh. Saberov, N. I. Korotkikh, A. S. Avksentiev, V. I. Yenya, G. F. Rayenko
{"title":"Catalytic Properties of Sterically Shielded Carbene Complexes of Palladium in C–C and C–N Coupling Reactions of Haloarenes","authors":"V. Sh. Saberov,&nbsp;N. I. Korotkikh,&nbsp;A. S. Avksentiev,&nbsp;V. I. Yenya,&nbsp;G. F. Rayenko","doi":"10.1007/s11237-024-09801-z","DOIUrl":null,"url":null,"abstract":"<p>New carbene complex catalysts based on palladium chloride, including PEPPSI-complexes (PEPPSI = Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation), have been synthesized. These catalysts show high efficiency in Buchwald–Hartwig C–N cross-coupling between aryl chlorides/bromides and amines, including sterically shielded reagents, and high efficiency in the Suzuki–Miyaura C–C cross-coupling reaction, where their use results in the formation of several tetra-ortho-substituted biaryls at very low amounts of catalyst under mild conditions. Modification of the catalyst structure to the PEPPSI complex leads to an unexpected decrease in activity in the Buchwald–Hartwig amination, in contrast to the Suzuki–Miyaura reaction, in which the PEPPSI complex showed greater activity in some cases.</p>","PeriodicalId":796,"journal":{"name":"Theoretical and Experimental Chemistry","volume":null,"pages":null},"PeriodicalIF":0.7000,"publicationDate":"2024-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Theoretical and Experimental Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s11237-024-09801-z","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0

Abstract

New carbene complex catalysts based on palladium chloride, including PEPPSI-complexes (PEPPSI = Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation), have been synthesized. These catalysts show high efficiency in Buchwald–Hartwig C–N cross-coupling between aryl chlorides/bromides and amines, including sterically shielded reagents, and high efficiency in the Suzuki–Miyaura C–C cross-coupling reaction, where their use results in the formation of several tetra-ortho-substituted biaryls at very low amounts of catalyst under mild conditions. Modification of the catalyst structure to the PEPPSI complex leads to an unexpected decrease in activity in the Buchwald–Hartwig amination, in contrast to the Suzuki–Miyaura reaction, in which the PEPPSI complex showed greater activity in some cases.

Abstract Image

Abstract Image

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
卤代烃 C-C 和 C-N 偶联反应中钯的立体屏蔽碳烯配合物的催化特性
我们合成了基于氯化钯的新型碳烯络合物催化剂,包括 PEPPSI-络合物(PEPPSI = Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation)。这些催化剂在芳基氯化物/溴化物与胺(包括立体屏蔽试剂)之间的 Buchwald-Hartwig C-N 交叉偶联反应中表现出高效率,在 Suzukii-Miyaura C-C 交叉偶联反应中也表现出高效率。改变 PEPPSI 复合物的催化剂结构会导致布赫瓦尔德-哈特维格胺化反应的活性意外降低,这与铃木-宫浦反应形成鲜明对比,在某些情况下,PEPPSI 复合物显示出更高的活性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
来源期刊
Theoretical and Experimental Chemistry
Theoretical and Experimental Chemistry CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
1.60
自引率
10.00%
发文量
30
审稿时长
6-12 weeks
期刊介绍: Theoretical and Experimental Chemistry is a journal for the rapid publication of research communications and reviews on modern problems of physical chemistry such as: a) physicochemical bases, principles, and methods for creation of novel processes, compounds, and materials; b) physicochemical principles of chemical process control, influence of external physical forces on chemical reactions; c) physical nanochemistry, nanostructures and nanomaterials, functional nanomaterials, size-dependent properties of materials.
期刊最新文献
Initiation of Radical-Chain Aerobic Oxidation of Cumene by Potassium Permanganate and N-Hydroxysuccinimide Spin-Orbit Interaction During the Activation of Molecular Oxygen by Oxidases and Cofactor-Free Oxygenases: A Review Electrochemical Properties of Composites Based on Carbon Nanomaterials: A Review High-Temperature Spiro-(1,1′)-Bipyrrolidinium Tetrafluoroborate-Based Organic Electrolytes for Supercapacitors Vapor-Phase Carbonylation of Methanol with the Obtaining of Acetyls on Solid-Phase Catalysts: A 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
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 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 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1