Silanes a Versatile Hydride Source for Ni–H Chemistry: A Promising Tool for π-Hydro Functionalization

IF 4.6 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Chemistry Frontiers Pub Date : 2024-06-07 DOI:10.1039/d4qo00860j
Yafia Kousin Mirza, Partha Sarathi Bera, Sachin Mohite, Ajeet Kumar Pandey, Milan Bera
{"title":"Silanes a Versatile Hydride Source for Ni–H Chemistry: A Promising Tool for π-Hydro Functionalization","authors":"Yafia Kousin Mirza, Partha Sarathi Bera, Sachin Mohite, Ajeet Kumar Pandey, Milan Bera","doi":"10.1039/d4qo00860j","DOIUrl":null,"url":null,"abstract":"Silanes, a simple and common hydride source, are emphasized for their chemical stability, neat and easy-to-handle and usually not requiring any precautions upon activation by nickel catalysis. Their hydride donor nature, reacted with ligand tailored nickel complex generates reactive Ni-H species, which is normally more prone to facile addition to the π-bond, thus generating the organonickel intermediate, which can undergo variety of sequential cross-coupling reactions. Notably, recent developments have brought to the forefront π-hydrofunctionalization reactions facilitated by Ni-H catalysis. In addition, the exploitation of suitable chiral ligands has paved the way for the realization of asymmetric hydrofunctionalization reactions in the realm of π-bonds. This review aims to provide an in-depth exploration of the latest achievements in C-C and C-heteroatom bond formations through silane mediated hydrofunctionalization catalyzed by nickel hydride. In particular, the NiH/ligand-catalytic system exhibits remarkable reactivity with π-substrates including alkenes, alkynes, and allenes. A thorough mechanistic understanding of these processes offers insights into the trends and future direction in drive innovation in catalyst design, fine tune reaction systems, and development of new cross-coupling reactions with π-substrates.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-06-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4qo00860j","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

Abstract

Silanes, a simple and common hydride source, are emphasized for their chemical stability, neat and easy-to-handle and usually not requiring any precautions upon activation by nickel catalysis. Their hydride donor nature, reacted with ligand tailored nickel complex generates reactive Ni-H species, which is normally more prone to facile addition to the π-bond, thus generating the organonickel intermediate, which can undergo variety of sequential cross-coupling reactions. Notably, recent developments have brought to the forefront π-hydrofunctionalization reactions facilitated by Ni-H catalysis. In addition, the exploitation of suitable chiral ligands has paved the way for the realization of asymmetric hydrofunctionalization reactions in the realm of π-bonds. This review aims to provide an in-depth exploration of the latest achievements in C-C and C-heteroatom bond formations through silane mediated hydrofunctionalization catalyzed by nickel hydride. In particular, the NiH/ligand-catalytic system exhibits remarkable reactivity with π-substrates including alkenes, alkynes, and allenes. A thorough mechanistic understanding of these processes offers insights into the trends and future direction in drive innovation in catalyst design, fine tune reaction systems, and development of new cross-coupling reactions with π-substrates.
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
硅烷是镍氢化学的多功能氢化物源:π-氢功能化的理想工具
硅烷是一种简单而常见的氢化物来源,因其化学性质稳定、纯净、易于处理以及在镍催化活化时通常无需采取任何预防措施而受到重视。它们具有氢化物供体性质,与配体定制的镍络合物反应后会产生活性 Ni-H 物种,通常更容易与 π 键发生加成反应,从而生成有机镍中间体,该中间体可发生各种连续的交叉偶联反应。值得注意的是,最近的发展已将 Ni-H 催化下的π-氢功能化反应推到了前沿。此外,利用合适的手性配体为实现π键领域的不对称氢官能化反应铺平了道路。本综述旨在深入探讨在氢化镍催化下,通过硅烷介导的氢官能化反应形成 C-C 和 C-heteroatom 键的最新成果。特别是,氢化镍/配体催化体系在与π基质(包括烯、炔和烯烃)发生反应时表现出显著的活性。对这些过程的透彻机理理解,有助于深入了解推动催化剂设计创新、微调反应体系以及开发以 π 为底物的新型交叉偶联反应的趋势和未来方向。
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
Organic Chemistry Frontiers
Organic Chemistry Frontiers CHEMISTRY, ORGANIC-
CiteScore
7.90
自引率
11.10%
发文量
686
审稿时长
1 months
期刊介绍: Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
期刊最新文献
A Ligand-assisted Manganese-enabled Direct C-H Difluoromethylation of Arenes Photoredox-Enabled Ring-Opening of Cyclobutanes via the Formation of a Carbon Radical Asymmetric Synthesis of 1H-pyrazolo[3,4-b]pyridine Analogues Catalyzed by Chiral-at-Metal Rh(III) Complexes Total Synthesis of (‒)-Deglycocadambine Copper-Catalyzed Allenynylative C–P Couplings of Diynylic Acetates with Hydrophosphoryl Compounds Leading to Phosphorylated Allenynes
×
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
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