• 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

铁催化烯丙醇与异丙醇的转移氢化反应

Iron-Catalyzed Transfer Hydrogenation of Allylic Alcohols with Isopropanol.

作者信息

Bari Md Abdul, Elsherbeni Salma A, Maqbool Tahir, Latham Daniel E, Gushlow Edward B, Harper Emily J, Morrill Louis C

机构信息

Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, United Kingdom.

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Tanta University, Tanta 31527, Egypt.

出版信息

J Org Chem. 2024 Oct 4;89(19):14571-14576. doi: 10.1021/acs.joc.4c01701. Epub 2024 Sep 25.

DOI:10.1021/acs.joc.4c01701
PMID:39320102
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11459429/
Abstract

Herein, we report an iron-catalyzed transfer hydrogenation of allylic alcohols. The operationally simple protocol employs a well-defined bench stable (cyclopentadienone)iron(0) carbonyl complex as a precatalyst in combination with KCO (4 mol %) and isopropanol as the hydrogen donor. A diverse range of allylic alcohols undergo transfer hydrogenation to form the corresponding alcohols in good yields (33 examples, ≤83% isolated yield). The scope and limitations of the method have been investigated, and experiments that shed light on the reaction mechanism have been conducted.

摘要

在此，我们报道了一种铁催化的烯丙醇转移氢化反应。该操作简单的方法使用一种定义明确、易于保存的（环戊二烯酮）铁（0）羰基配合物作为预催化剂，与碳酸钾（4 mol%）和异丙醇作为氢供体相结合。多种烯丙醇可进行转移氢化反应，以良好的产率生成相应的醇（33个实例，分离产率≤83%）。我们研究了该方法的适用范围和局限性，并进行了有助于阐明反应机理的实验。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d805/11459429/41a4ba7bd821/jo4c01701_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d805/11459429/d84de235d9fb/jo4c01701_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d805/11459429/9be33815e51d/jo4c01701_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d805/11459429/1635c32ce1ea/jo4c01701_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d805/11459429/41a4ba7bd821/jo4c01701_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d805/11459429/d84de235d9fb/jo4c01701_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d805/11459429/9be33815e51d/jo4c01701_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d805/11459429/1635c32ce1ea/jo4c01701_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d805/11459429/41a4ba7bd821/jo4c01701_0004.jpg

相似文献

1
Iron-Catalyzed Transfer Hydrogenation of Allylic Alcohols with Isopropanol.铁催化烯丙醇与异丙醇的转移氢化反应
J Org Chem. 2024 Oct 4;89(19):14571-14576. doi: 10.1021/acs.joc.4c01701. Epub 2024 Sep 25.
2
Iron-Catalyzed Borrowing Hydrogen β-(sp)-Methylation of Alcohols.铁催化醇的借氢β-(sp)甲基化反应
ACS Catal. 2019 Sep 6;9(9):8575-8580. doi: 10.1021/acscatal.9b02461. Epub 2019 Aug 21.
3
One-Pot Conversion of Allylic Alcohols to α-Methyl Ketones via Iron-Catalyzed Isomerization-Methylation.通过铁催化的异构化-甲基化反应将烯丙醇一锅法转化为α-甲基酮
Org Lett. 2019 Oct 4;21(19):7914-7918. doi: 10.1021/acs.orglett.9b02900. Epub 2019 Sep 19.
4
Iron-Catalyzed Borrowing Hydrogen C-Alkylation of Oxindoles with Alcohols.铁催化的氧化吲哚与醇的借氢C-烷基化反应
ChemSusChem. 2019 Jun 7;12(11):2345-2349. doi: 10.1002/cssc.201900799. Epub 2019 May 7.
5
Ruthenium-catalyzed C-C bond forming transfer hydrogenation: carbonyl allylation from the alcohol or aldehyde oxidation level employing acyclic 1,3-dienes as surrogates to preformed allyl metal reagents.钌催化的碳-碳键形成转移氢化反应：以无环1,3-二烯作为预制烯丙基金属试剂的替代物，从醇或醛氧化态进行羰基烯丙基化反应。
J Am Chem Soc. 2008 May 21;130(20):6338-9. doi: 10.1021/ja801213x. Epub 2008 Apr 29.
6
Enantioselective iridium-catalyzed carbonyl allylation from the alcohol or aldehyde oxidation level via transfer hydrogenative coupling of allyl acetate: departure from chirally modified allyl metal reagents in carbonyl addition.通过乙酸烯丙酯的转移氢化偶联，从醇或醛氧化水平进行对映选择性铱催化的羰基烯丙基化反应：在羰基加成反应中背离手性修饰的烯丙基金属试剂。
J Am Chem Soc. 2008 Nov 5;130(44):14891-9. doi: 10.1021/ja805722e. Epub 2008 Oct 8.
7
Asymmetric Hydrogenation of Racemic Allylic Alcohols via an Isomerization-Dynamic Kinetic Resolution Cascade.外消旋烯丙醇的不对称氢化通过异构化-动态动力学拆分级联反应。
J Org Chem. 2022 Mar 4;87(5):3804-3809. doi: 10.1021/acs.joc.1c02916. Epub 2022 Jan 18.
8
Direct Synthesis of Pyrrolo[1,2-α]quinoxalines Iron-Catalyzed Transfer Hydrogenation between 1-(2-Nitrophenyl)pyrroles and Alcohols.吡咯并[1,2-α]喹喔啉的直接合成 铁催化 1-(2-硝基苯基)吡咯与醇之间的转移氢化。
J Org Chem. 2020 Dec 4;85(23):15314-15324. doi: 10.1021/acs.joc.0c02145. Epub 2020 Oct 29.
9
Synthetic scope of Ru(OH)x/Al2O3-catalyzed hydrogen-transfer reactions: an application to reduction of allylic alcohols by a sequential process of isomerization/Meerwein-Ponndorf-Verley-type reduction.Ru(OH)x/Al₂O₃催化氢转移反应的合成范围：通过异构化/麦尔外因-彭多夫-韦利型还原的连续过程应用于烯丙醇的还原。
Chemistry. 2008;14(13):4104-9. doi: 10.1002/chem.200701917.
10
Iridium-Catalyzed Selective Isomerization of Primary Allylic Alcohols.铱催化的伯烯丙醇的选择性异构化反应。
Acc Chem Res. 2016 Jun 21;49(6):1232-41. doi: 10.1021/acs.accounts.6b00144. Epub 2016 May 9.

本文引用的文献

1
Blue-Light Induced Iron-Catalyzed Synthesis of γ,δ-Unsaturated Ketones.蓝光诱导铁催化合成γ,δ-不饱和酮
ChemSusChem. 2024 Apr 8;17(7):e202301472. doi: 10.1002/cssc.202301472. Epub 2023 Dec 8.
2
Enantioconvergent transformations of secondary alcohols through borrowing hydrogen catalysis.通过借氢催化实现仲醇的对映汇聚式转化。
Chem Soc Rev. 2023 Aug 14;52(16):5541-5562. doi: 10.1039/d3cs00424d.
3
Ruthenium-catalysed α-prenylation of ketones using prenol.钌催化的使用异戊烯醇对酮进行α-异戊烯基化反应
Org Biomol Chem. 2023 Jan 4;21(2):273-278. doi: 10.1039/d2ob01882a.
4
Recent advances in /-alkylation with alcohols through hydride transfer strategies.通过氢化物转移策略实现醇的/ - 烷基化的最新进展。
Org Biomol Chem. 2022 Oct 12;20(39):7713-7745. doi: 10.1039/d2ob00706a.
5
Fe-Catalyzed Amidation of Allylic Alcohols by Borrowing Hydrogen Catalysis.铁催化的烯丙醇通过借氢催化的酰胺化反应。
Chemistry. 2022 Oct 26;28(60):e202201829. doi: 10.1002/chem.202201829. Epub 2022 Aug 26.
6
Blue-Light-Induced Iron-Catalyzed α-Alkylation of Ketones.蓝光诱导铁催化的酮的α-烷基化反应
Org Lett. 2022 Aug 5;24(30):5584-5589. doi: 10.1021/acs.orglett.2c02233. Epub 2022 Jul 27.
7
Stereodivergent Construction of 1,4-Nonadjacent Stereocenters via Hydroalkylation of Racemic Allylic Alcohols Enabled by Copper/Ruthenium Relay Catalysis.通过铜/钌接力催化实现的外消旋烯丙醇的氢烷基化反应立体发散构建1,4-非相邻立体中心
Angew Chem Int Ed Engl. 2022 Sep 5;61(36):e202206517. doi: 10.1002/anie.202206517. Epub 2022 Jul 26.
8
Catalytic Formal Hydroamination of Allylic Alcohols Using Manganese PNP-Pincer Complexes.使用锰PNP钳形配合物对烯丙醇进行催化形式氢胺化反应。
Adv Synth Catal. 2021 Sep 7;363(17):4177-4181. doi: 10.1002/adsc.202100081. Epub 2021 Mar 17.
9
Borrowing Hydrogen for Organic Synthesis.用于有机合成的氢借用。
ACS Cent Sci. 2021 Apr 28;7(4):570-585. doi: 10.1021/acscentsci.1c00125. Epub 2021 Mar 25.
10
(Cyclopentadienone)iron Complexes: Synthesis, Mechanism and Applications in Organic Synthesis.茂铁配合物：合成、机理及在有机合成中的应用。
Chem Asian J. 2021 Jul 5;16(13):1703-1724. doi: 10.1002/asia.202100400. Epub 2021 Jun 1.