• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

将手性受阻路易斯酸碱对引入具有定制微环境的金属有机框架用于非均相对映选择性和化学选择性氢化反应。

Incorporation of Chiral Frustrated Lewis Pair into Metal-Organic Framework with Tailored Microenvironment for Heterogeneous Enantio- and Chemoselective Hydrogenation.

作者信息

Zhang Yin, Jiang Yao, Nafady Ayman, Tang Zhiyong, Al-Enizi Abdullah M, Tan Kui, Ma Shengqian

机构信息

Department of Chemistry, University of North Texas, Denton, Texas 76201, United States.

School of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei 230009, People's Republic of China.

出版信息

ACS Cent Sci. 2023 Jul 27;9(8):1692-1701. doi: 10.1021/acscentsci.3c00637. eCollection 2023 Aug 23.

DOI:10.1021/acscentsci.3c00637
PMID:37637733
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10451035/
Abstract

The development of efficient heterogeneous catalysts with multiselectivity (e.g., enantio- and chemoselectivity) has long been sought after but with limited progress being made so far. To achieve enantio- and chemoselectivity in a heterogeneous system, as inspired by enzymes, we illustrate herein an approach of creating an enzyme-mimic region (EMR) within the nanospace of a metal-organic framework (MOF) as exemplified in the context of incorporating a chiral frustrated Lewis pair (CFLP) into a MOF with a tailored pore environment. Due to the high density of the EMR featuring the active site of CFLP and auxiliary sites of the hydroxyl group/open metal site within the vicinity of CFLP, the resultant EMR@MOF demonstrated excellent catalysis performance in heterogeneous hydrogenation of α,β-unsaturated imines to afford chiral β-unsaturated amines with high yields and high enantio- and chemoselectivity. The role of the hydroxyl group/open metal site in regulating chemoselectivity was proved by the observation of a catalyst-substrate interaction experimentally, which was also rationalized by computational results. This work not only contributes a MOF as a new platform for multiselective catalysis but also opens a promising avenue to develop heterogeneous catalysts with multiselectivity for challenging yet important transformations.

摘要

高效的具有多种选择性(如对映选择性和化学选择性)的多相催化剂的开发一直是人们长期追求的目标,但迄今为止进展有限。受酶的启发,为了在多相体系中实现对映选择性和化学选择性,我们在此阐述了一种在金属有机框架(MOF)的纳米空间内创建类酶区域(EMR)的方法,以将手性受阻路易斯对(CFLP)纳入具有定制孔环境的MOF为例进行说明。由于EMR具有高密度的CFLP活性位点以及CFLP附近的羟基/开放金属位点辅助位点,所得的EMR@MOF在α,β-不饱和亚胺的多相氢化反应中表现出优异的催化性能,能够高产率地提供具有高对映选择性和化学选择性的手性β-不饱和胺。通过实验观察到的催化剂-底物相互作用证明了羟基/开放金属位点在调节化学选择性方面的作用,计算结果也对此进行了合理的解释。这项工作不仅为多选择性催化贡献了一个作为新平台的MOF,而且为开发用于挑战性但重要转化的具有多选择性的多相催化剂开辟了一条有前途的途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e5eb/10451035/2dfff26c75fc/oc3c00637_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e5eb/10451035/18ead399c365/oc3c00637_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e5eb/10451035/4406866c4456/oc3c00637_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e5eb/10451035/e6ec79388cc9/oc3c00637_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e5eb/10451035/d8a71bc5fdcc/oc3c00637_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e5eb/10451035/2dfff26c75fc/oc3c00637_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e5eb/10451035/18ead399c365/oc3c00637_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e5eb/10451035/4406866c4456/oc3c00637_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e5eb/10451035/e6ec79388cc9/oc3c00637_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e5eb/10451035/d8a71bc5fdcc/oc3c00637_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e5eb/10451035/2dfff26c75fc/oc3c00637_0004.jpg

相似文献

1
Incorporation of Chiral Frustrated Lewis Pair into Metal-Organic Framework with Tailored Microenvironment for Heterogeneous Enantio- and Chemoselective Hydrogenation.将手性受阻路易斯酸碱对引入具有定制微环境的金属有机框架用于非均相对映选择性和化学选择性氢化反应。
ACS Cent Sci. 2023 Jul 27;9(8):1692-1701. doi: 10.1021/acscentsci.3c00637. eCollection 2023 Aug 23.
2
Chiral Frustrated Lewis Pair@Metal-Organic Framework as a New Platform for Heterogeneous Asymmetric Hydrogenation.手性受阻路易斯酸碱对@金属有机框架作为多相不对称氢化的新平台
Angew Chem Int Ed Engl. 2023 Jan 9;62(2):e202213399. doi: 10.1002/anie.202213399. Epub 2022 Dec 7.
3
Promoting Frustrated Lewis Pairs for Heterogeneous Chemoselective Hydrogenation via the Tailored Pore Environment within Metal-Organic Frameworks.通过金属有机框架内定制的孔环境促进受挫路易斯对用于多相化学选择性氢化反应
Angew Chem Int Ed Engl. 2019 May 27;58(22):7420-7424. doi: 10.1002/anie.201903763. Epub 2019 Apr 17.
4
Metal-Free Heterogeneous Asymmetric Hydrogenation of Olefins Promoted by Chiral Frustrated Lewis Pair Framework.手性受阻路易斯对框架促进的烯烃无金属多相不对称氢化反应
J Am Chem Soc. 2024 Jan 10;146(1):979-987. doi: 10.1021/jacs.3c11607. Epub 2023 Dec 20.
5
Coordination Defect-Induced Frustrated Lewis Pairs in Polyoxo-metalate-Based Metal-Organic Frameworks for Efficient Catalytic Hydrogenation.基于多金属氧酸盐的金属有机框架中配位缺陷诱导的受阻路易斯酸碱对用于高效催化氢化反应
Angew Chem Int Ed Engl. 2023 Sep 11;62(37):e202309030. doi: 10.1002/anie.202309030. Epub 2023 Aug 3.
6
Catalytic hydrogenation with frustrated Lewis pairs: selectivity achieved by size-exclusion design of Lewis acids.受阻路易斯酸碱对催化氢化反应:通过路易斯酸的尺寸排阻设计实现选择性。
Chemistry. 2012 Jan 9;18(2):574-85. doi: 10.1002/chem.201102438. Epub 2011 Dec 12.
7
Frustrated Lewis Pairs Catalyzed Asymmetric Metal-Free Hydrogenations and Hydrosilylations.受阻路易斯对催化的不对称非均相氢化和硅氢化反应。
Acc Chem Res. 2018 Jan 16;51(1):191-201. doi: 10.1021/acs.accounts.7b00530. Epub 2017 Dec 15.
8
Porous Frustrated Lewis Pairs Catalyst Constructed on Defective Zirconium-Based Metal-Organic Frameworks for Hydrogenation Reactions with H.基于缺陷锆基金属有机框架构建的多孔受阻路易斯酸碱对催化剂用于与氢气的氢化反应
Inorg Chem. 2024 Aug 26;63(34):16011-16017. doi: 10.1021/acs.inorgchem.4c02470. Epub 2024 Aug 15.
9
Introducing Frustrated Lewis Pairs to Metal-Organic Framework for Selective Hydrogenation of -Heterocycles.将受阻路易斯酸碱对引入金属有机框架用于杂环化合物的选择性氢化
J Am Chem Soc. 2023 Jul 12;145(27):14994-15000. doi: 10.1021/jacs.3c04929. Epub 2023 Jun 29.
10
New Opportunities in Metal-Organic Framework Catalysis: From Bifunctional to Frustrated Lewis Pairs Catalysis.金属有机框架催化的新机遇:从双功能催化到受阻路易斯酸碱对催化
Chemistry. 2023 Jul 6;29(38):e202204016. doi: 10.1002/chem.202204016. Epub 2023 Jun 6.

引用本文的文献

1
Pore engineering in metal-organic frameworks and covalent organic frameworks: strategies and applications.金属有机框架和共价有机框架中的孔工程:策略与应用
Chem Sci. 2025 Jun 14. doi: 10.1039/d5sc01635e.
2
Exploring Supramolecular Frustrated Lewis Pairs.探索超分子受阻路易斯酸碱对
Chempluschem. 2025 May;90(5):e202400725. doi: 10.1002/cplu.202400725. Epub 2025 Feb 11.
3
Heterogeneous Frustrated Lewis Pair Catalysts: Rational Structure Design and Mechanistic Elucidation Based on Intrinsic Properties of Supports.非均相受阻路易斯酸碱对催化剂:基于载体固有性质的合理结构设计与机理阐释

本文引用的文献

1
Introducing Frustrated Lewis Pairs to Metal-Organic Framework for Selective Hydrogenation of -Heterocycles.将受阻路易斯酸碱对引入金属有机框架用于杂环化合物的选择性氢化
J Am Chem Soc. 2023 Jul 12;145(27):14994-15000. doi: 10.1021/jacs.3c04929. Epub 2023 Jun 29.
2
Construction of Monophosphine-Metal Complexes in Privileged Diphosphine-Based Covalent Organic Frameworks for Catalytic Asymmetric Hydrogenation.基于特权二膦的共价有机框架中用于催化不对称氢化的单膦-金属配合物的构建
J Am Chem Soc. 2023 Mar 22;145(11):6100-6111. doi: 10.1021/jacs.2c11037. Epub 2023 Mar 10.
3
Asymmetric Reduction of Quinolines: A Competition between Enantioselective Transfer Hydrogenation and Racemic Borane Catalysis.
Acc Chem Res. 2025 Feb 18;58(4):555-569. doi: 10.1021/acs.accounts.4c00683. Epub 2025 Jan 28.
4
CO-Free Aminocarbonylation of Terminal Alkynes Catalyzed by Synergistic Effect From Metal-Organic Frameworks.金属有机框架协同效应催化端炔的无钴氨羰基化反应
Adv Sci (Weinh). 2024 Nov;11(41):e2405308. doi: 10.1002/advs.202405308. Epub 2024 Sep 5.
5
Defect-engineered chiral metal-organic frameworks.缺陷工程化手性金属有机框架
Mikrochim Acta. 2024 Jul 10;191(8):458. doi: 10.1007/s00604-024-06534-7.
6
Engineering Frustrated Lewis Pair Active Sites in Porous Organic Scaffolds for Catalytic CO Hydrogenation.在多孔有机骨架中构建受阻路易斯酸碱对活性位点用于催化CO加氢反应
J Am Chem Soc. 2024 Jun 12;146(23):15806-15814. doi: 10.1021/jacs.4c01890. Epub 2024 May 30.
7
Biomimetic Chiral Nanomaterials with Selective Catalysis Activity.具有选择性催化活性的仿生手性纳米材料。
Adv Sci (Weinh). 2024 Jun;11(23):e2306979. doi: 10.1002/advs.202306979. Epub 2024 Apr 1.
不对称喹啉还原:对映选择性转移氢化和外消旋硼烷催化之间的竞争。
J Org Chem. 2023 Mar 3;88(5):3335-3339. doi: 10.1021/acs.joc.2c02905. Epub 2023 Feb 17.
4
Homochiral Porous Metal-Organic Polyhedra with Multiple Kinds of Vertices.具有多种顶点的手性多孔金属有机多面体
J Am Chem Soc. 2023 Feb 1;145(4):2561-2571. doi: 10.1021/jacs.2c12424. Epub 2023 Jan 17.
5
Chiral Frustrated Lewis Pair@Metal-Organic Framework as a New Platform for Heterogeneous Asymmetric Hydrogenation.手性受阻路易斯酸碱对@金属有机框架作为多相不对称氢化的新平台
Angew Chem Int Ed Engl. 2023 Jan 9;62(2):e202213399. doi: 10.1002/anie.202213399. Epub 2022 Dec 7.
6
Conformational Control of Organocatalyst in Strongly Brønsted-Acidic Metal-Organic Frameworks for Enantioselective Catalysis.强酸性金属有机骨架中有机催化剂的构象控制用于手性催化。
Angew Chem Int Ed Engl. 2023 Jan 9;62(2):e202214748. doi: 10.1002/anie.202214748. Epub 2022 Dec 2.
7
Asymmetric Hydrogenation by Relay Catalysis with FLPs and CPAs: Stereodivergent Synthesis of 3-Substituted Flavanones.手性 FLP 和 CPA 接力催化的不对称氢化反应:3-取代黄酮的立体发散合成。
J Org Chem. 2022 Aug 5;87(15):10544-10549. doi: 10.1021/acs.joc.2c01278. Epub 2022 Jul 7.
8
Bioinspired Supercharging of Photoredox Catalysis for Applications in Energy and Chemical Manufacturing.仿生光氧化还原催化强化及其在能源与化学制造中的应用。
Acc Chem Res. 2022 May 17;55(10):1423-1434. doi: 10.1021/acs.accounts.2c00083. Epub 2022 Apr 26.
9
Chiral Metal-Organic Frameworks.手性金属有机框架
Chem Rev. 2022 May 11;122(9):9078-9144. doi: 10.1021/acs.chemrev.1c00740. Epub 2022 Mar 28.
10
Asymmetric Intramolecular Hydroalkoxylation of 2-Vinylbenzyl Alcohols with Chiral Boro-Phosphates.手性硼酸磷酸酯催化2-乙烯基苄醇的不对称分子内氢烷氧基化反应
Angew Chem Int Ed Engl. 2022 May 16;61(21):e202200100. doi: 10.1002/anie.202200100. Epub 2022 Mar 23.