• 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

醇酸酯作为转移氢烷基化试剂及其在亚胺催化转化为烷基胺中的应用。

Alkyl Formates as Transfer Hydroalkylation Reagents and Their Use in the Catalytic Conversion of Imines to Alkylamines.

机构信息

Université Paris-Saclay, CEA, CNRS, NIMBE, 91191, Gif-sur-Yvette, France.

出版信息

Angew Chem Int Ed Engl. 2023 Jan 2;62(1):e202214069. doi: 10.1002/anie.202214069. Epub 2022 Nov 30.

DOI:10.1002/anie.202214069
PMID:36259458
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10100357/
Abstract

Easily accessible via a simple esterification of alcohols with formic acid, alkyl formates are used as a novel class of transfer hydroalkylation reagents, CO acting as a traceless linker. As a proof-of-concept, their reactivity in the transfer hydroalkylation of imines is investigated, using a ruthenium-based catalyst and LiI as promoter to cleave the C-O σ-bond of the formate scaffold. Providing tertiary amines, the reaction displays a divergent regioselectivity compared to previously reported transfer hydroalkylation strategies.

摘要

通过醇与甲酸的简单酯化反应即可轻松获得，烷基甲酸酯被用作一类新型的转移氢烷基化试剂，CO 充当无痕迹连接体。作为概念验证，使用基于钌的催化剂和碘化锂作为促进剂来裂解甲酸酯支架的 C-O σ 键，研究了它们在亚胺的转移氢烷基化反应中的反应性。提供叔胺时，与以前报道的转移氢烷基化策略相比，该反应表现出不同的区域选择性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d8/10100357/4bdff7cc4aae/ANIE-62-0-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d8/10100357/88d871cfb7b9/ANIE-62-0-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d8/10100357/11b34debaf26/ANIE-62-0-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d8/10100357/c4c71ac6d43d/ANIE-62-0-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d8/10100357/0be384eb3c92/ANIE-62-0-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d8/10100357/1bda3fbb6496/ANIE-62-0-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d8/10100357/4bdff7cc4aae/ANIE-62-0-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d8/10100357/88d871cfb7b9/ANIE-62-0-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d8/10100357/11b34debaf26/ANIE-62-0-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d8/10100357/c4c71ac6d43d/ANIE-62-0-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d8/10100357/0be384eb3c92/ANIE-62-0-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d8/10100357/1bda3fbb6496/ANIE-62-0-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e0d8/10100357/4bdff7cc4aae/ANIE-62-0-g002.jpg

相似文献

1
Alkyl Formates as Transfer Hydroalkylation Reagents and Their Use in the Catalytic Conversion of Imines to Alkylamines.醇酸酯作为转移氢烷基化试剂及其在亚胺催化转化为烷基胺中的应用。
Angew Chem Int Ed Engl. 2023 Jan 2;62(1):e202214069. doi: 10.1002/anie.202214069. Epub 2022 Nov 30.
2
Enantioselective synthesis of alcohols and amines by iridium-catalyzed hydrogenation, transfer hydrogenation, and related processes.通过铱催化氢化、转移氢化和相关过程对醇和胺进行对映选择性合成。
Chemistry. 2013 Jun 3;19(23):7274-302. doi: 10.1002/chem.201202836. Epub 2013 Apr 19.
3
Switch in Selectivity for Formal Hydroalkylation of 1,3-Dienes and Enynes with Simple Hydrazones.1,3 - 二烯和烯炔与简单腙的形式氢烷基化反应选择性的转变
Angew Chem Int Ed Engl. 2020 Apr 16;59(16):6466-6472. doi: 10.1002/anie.201915875. Epub 2020 Feb 28.
4
Regioselective Hydroalkylation of Vinylarenes by Cooperative Cu and Ni Catalysis.铜镍协同催化实现乙烯基芳烃的区域选择性氢烷基化反应
Angew Chem Int Ed Engl. 2022 Jan 21;61(4):e202112390. doi: 10.1002/anie.202112390. Epub 2021 Dec 9.
5
Ruthenium-catalyzed transfer hydrogenation of imines by propan-2-ol in benzene.钌催化下，苯中2-丙醇对亚胺的转移氢化反应。
Chemistry. 2002 Jul 2;8(13):2955-61. doi: 10.1002/1521-3765(20020703)8:13<2955::AID-CHEM2955>3.0.CO;2-Q.
6
Spherical BiO/ATO catalyst with N pre-reduction electrocatalytic reduction of CO to formic acid.具有氮预还原的球形BiO/ATO催化剂用于将CO电催化还原为甲酸。
J Environ Sci (China). 2024 Jun;140:331-340. doi: 10.1016/j.jes.2023.11.009. Epub 2023 Nov 21.
7
Ruthenium-catalyzed alkylation of indoles with tertiary amines by oxidation of a sp3 C-H bond and Lewis acid catalysis.钌催化的三级胺与吲哚的 sp3 C-H 键氧化烷基化反应及路易斯酸催化作用。
Chemistry. 2010 May 17;16(19):5723-35. doi: 10.1002/chem.200902387.
8
Aqueous Biphasic Systems for the Synthesis of Formates by Catalytic CO Hydrogenation: Integrated Reaction and Catalyst Separation for CO -Scrubbing Solutions.用于催化CO加氢合成甲酸盐的双水相体系：用于CO洗涤溶液的集成反应与催化剂分离
ChemSusChem. 2017 Mar 22;10(6):1085-1093. doi: 10.1002/cssc.201601814. Epub 2017 Feb 17.
9
Role of Intermolecular Interactions in the Catalytic Reaction of Formic Acid on Cu(111).分子间相互作用在甲酸在 Cu(111)上的催化反应中的作用。
Small. 2021 May;17(20):e2008010. doi: 10.1002/smll.202008010. Epub 2021 Mar 23.
10
Catalytic Hydrotreatment of Humins in Mixtures of Formic Acid/2-Propanol with Supported Ruthenium Catalysts.负载型钌催化剂催化甲酸/2-丙醇混合物中腐殖质的加氢处理
ChemSusChem. 2016 May 10;9(9):951-61. doi: 10.1002/cssc.201501371. Epub 2016 Feb 2.

引用本文的文献

1
Catalytic Reduction of Imines with Silylformates: Formation of Silyl Carbamates through CO Insertion.用甲硅烷基甲酸酯催化还原亚胺：通过CO插入形成甲硅烷基氨基甲酸酯。
Chemistry. 2025 Mar 12;31(15):e202403907. doi: 10.1002/chem.202403907. Epub 2025 Feb 5.

本文引用的文献

1
Bifunctional reagents in organic synthesis.有机合成中的双功能试剂。
Nat Rev Chem. 2021 May;5(5):301-321. doi: 10.1038/s41570-021-00266-5. Epub 2021 Apr 12.
2
Silyl formates as hydrosilane surrogates for the transfer hydrosilylation of ketones.硅基甲酸酯作为硅烷供体替代物在酮的转移氢化硅烷化反应中的应用。
Chem Commun (Camb). 2022 May 26;58(43):6308-6311. doi: 10.1039/d2cc00666a.
3
Hydroalkylation of Unactivated Olefins via Visible-Light-Driven Dual Hydrogen Atom Transfer Catalysis.可见光驱动双氢原子转移催化活化烯烃的氢烷基化反应。
J Am Chem Soc. 2021 Jul 28;143(29):11251-11261. doi: 10.1021/jacs.1c05852. Epub 2021 Jul 16.
4
Radical Hydroalkylation and Hydroacylation of Alkenes by the Use of Benzothiazoline under Thermal Conditions.热条件下利用苯并噻唑啉对烯烃进行自由基氢烷基化和氢酰化反应
J Org Chem. 2020 Oct 2;85(19):12715-12723. doi: 10.1021/acs.joc.0c01872. Epub 2020 Sep 21.
5
Iridium-Catalyzed Hydroalkylation of Aliphatic Alkenes with β-Ketoesters: Formal Hydroalkylation with Methyl Ketones.铱催化脂肪族烯烃与β-酮酯的氢烷基化反应：与甲基酮的形式氢烷基化反应
Org Lett. 2020 Aug 7;22(15):6187-6191. doi: 10.1021/acs.orglett.0c02291. Epub 2020 Jul 22.
6
Palladium-Catalyzed Formal Hydroalkylation of Aryl-Substituted Alkynes with Hydrazones.钯催化芳基取代炔烃与腙的形式氢烷基化反应。
Angew Chem Int Ed Engl. 2020 Aug 10;59(33):14009-14013. doi: 10.1002/anie.202005132. Epub 2020 Jun 4.
7
Benzothiazolines as radical transfer reagents: hydroalkylation and hydroacylation of alkenes by radical generation under photoirradiation conditions.苯并噻唑啉作为自由基转移试剂：在光照条件下通过自由基引发实现烯烃的氢烷基化和氢酰基化反应。
Chem Commun (Camb). 2019 Sep 17;55(75):11171-11174. doi: 10.1039/c9cc05336k.
8
Hantzsch esters: an emerging versatile class of reagents in photoredox catalyzed organic synthesis.Hantzsch 酯：光氧化还原催化有机合成中新兴的多功能试剂类。
Org Biomol Chem. 2019 Aug 7;17(29):6936-6951. doi: 10.1039/c9ob01289c. Epub 2019 Jul 3.
9
Alkylation Reactions of Azodicarboxylate Esters with 4-Alkyl-1,4-Dihydropyridines under Catalyst-Free Conditions.偶氮二甲酸酯与4-烷基-1,4-二氢吡啶在无催化剂条件下的烷基化反应
Org Lett. 2019 Jun 21;21(12):4642-4645. doi: 10.1021/acs.orglett.9b01537. Epub 2019 May 30.
10
A Redox-Active Nickel Complex that Acts as an Electron Mediator in Photochemical Giese Reactions.一种在光化学吉泽反应中充当电子媒介体的氧化还原活性镍配合物。
Angew Chem Int Ed Engl. 2019 Apr 1;58(15):4953-4957. doi: 10.1002/anie.201814497. Epub 2019 Mar 6.