• 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

镍催化芳基氟代硫酸酯与异氰酸酯的还原胺化反应:通过C-O键裂解合成酰胺

Nickel-Catalyzed Reductive Amidation of Aryl Fluorosulfates with Isocyanates: Synthesis of Amides via C-O Bond Cleavage.

作者信息

Qin Gan-Qi, Wang Jiao, Cao Xu-Rong, Chu Xue-Qiang, Zhou Xiaocong, Rao Weidong, Zhai Li-Xin, Miao Chengping, Shen Zhi-Liang

机构信息

Technical Institute of Fluorochemistry (TIF), School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.

College of Biological, Chemical Science and Engineering, Jiaxing University, 118 Jiahang Road, Jiaxing 314001, China.

出版信息

J Org Chem. 2024 Sep 20;89(18):13735-13743. doi: 10.1021/acs.joc.4c01399. Epub 2024 Aug 30.

DOI:10.1021/acs.joc.4c01399
PMID:39213645
Abstract

With the assistance of nickel as catalyst, 2,2'-bipyridine (bpy) as ligand, and manganese as reducing metal, the reductive amidation of isocyanates with readily accessible aryl fluorosulfates could be successfully accomplished. The reactions proceeded effectively via C-O bond activation in DMF at room temperature, enabling the facile synthesis of a range of structurally diverse amides in moderate to high yields with broad functionality compatibility. In addition, the synthetic usefulness of the method was further demonstrated by applying the reaction in scale-up synthesis and the late-stage functionalization of complex molecules with biological activities.

摘要

在镍作为催化剂、2,2'-联吡啶(bpy)作为配体以及锰作为还原金属的辅助下,异氰酸酯与易于获得的芳基氟硫酸盐的还原酰胺化反应能够成功实现。反应在室温下于N,N-二甲基甲酰胺(DMF)中通过C-O键活化有效地进行,能够以中等到高的产率轻松合成一系列结构多样的酰胺,且具有广泛的官能团兼容性。此外,通过将该反应应用于放大合成以及具有生物活性的复杂分子的后期官能化,进一步证明了该方法的合成实用性。

相似文献

1
Nickel-Catalyzed Reductive Amidation of Aryl Fluorosulfates with Isocyanates: Synthesis of Amides via C-O Bond Cleavage.镍催化芳基氟代硫酸酯与异氰酸酯的还原胺化反应:通过C-O键裂解合成酰胺
J Org Chem. 2024 Sep 20;89(18):13735-13743. doi: 10.1021/acs.joc.4c01399. Epub 2024 Aug 30.
2
Palladium-Catalyzed Esterification of Aryl Fluorosulfates with Aryl Formates.钯催化芳基氟代硫酸酯与芳基甲酸酯的酯化反应。
Molecules. 2024 Apr 26;29(9):1991. doi: 10.3390/molecules29091991.
3
Transamidation of Amides and Amidation of Esters by Selective N-C(O)/O-C(O) Cleavage Mediated by Air- and Moisture-Stable Half-Sandwich Nickel(II)-NHC Complexes.空气和水分稳定的半夹心镍(II)-NHC 配合物介导的酰胺的转酰胺化和酯的酰胺化反应,通过选择性 N-C(O)/O-C(O)裂解实现。
Molecules. 2021 Jan 2;26(1):188. doi: 10.3390/molecules26010188.
4
Nickel-catalyzed reductive amidation of aryl-triazine ethers.镍催化的芳基三嗪醚的还原酰胺化反应。
Chem Commun (Camb). 2020 Feb 13;56(13):1992-1995. doi: 10.1039/c9cc08727c.
5
Recent Advances in First-Row Transition Metal-Catalyzed Reductive Coupling Reactions for π-Bond Functionalization and C-Glycosylation.用于π键官能化和C-糖基化的第一行过渡金属催化还原偶联反应的最新进展
Acc Chem Res. 2023 Nov 21;56(22):3292-3312. doi: 10.1021/acs.accounts.3c00531. Epub 2023 Nov 2.
6
Cross-Couplings Using Aryl Ethers via C-O Bond Activation Enabled by Nickel Catalysts.镍催化剂促进的通过 C-O 键活化的芳基醚的交叉偶联反应。
Acc Chem Res. 2015 Jun 16;48(6):1717-26. doi: 10.1021/acs.accounts.5b00051. Epub 2015 Jun 3.
7
Decarbonylative Cross-Couplings: Nickel Catalyzed Functional Group Interconversion Strategies for the Construction of Complex Organic Molecules.脱羰交叉偶联反应:镍催化构建复杂有机分子的官能团相互转化策略
Acc Chem Res. 2018 May 15;51(5):1185-1195. doi: 10.1021/acs.accounts.8b00023. Epub 2018 Apr 13.
8
Acid-promoted chemoselective introduction of amide functionality onto aromatic compounds mediated by an isocyanate cation generated from carbamate.由氨基甲酸酯生成的异氰酸酯阳离子介导的、酸促进的酰胺官能团向芳香族化合物上的化学选择性引入。
Chem Asian J. 2014 Oct;9(10):2995-3004. doi: 10.1002/asia.201402625. Epub 2014 Aug 19.
9
Transition Metal-Catalyzed Regioselective Direct C-H Amidation: Interplay between Inner- and Outer-Sphere Pathways for Nitrene Cross-Coupling Reactions.过渡金属催化的区域选择性直接 C-H 酰胺化:氮宾交叉偶联反应中内界和外界途径的相互作用。
Acc Chem Res. 2022 Aug 2;55(15):2123-2137. doi: 10.1021/acs.accounts.2c00283. Epub 2022 Jul 19.
10
Selective Reductive Removal of Ester and Amide Groups from Arenes and Heteroarenes through Nickel-Catalyzed C-O and C-N Bond Activation.通过镍催化的 C-O 和 C-N 键活化,从芳烃和杂芳烃中选择性还原去除酯基和酰胺基。
Angew Chem Int Ed Engl. 2017 Mar 27;56(14):3972-3976. doi: 10.1002/anie.201612624. Epub 2017 Mar 21.