• 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

无催化剂的单重态氧促进的α-酮酸与游离胺的脱羧酰胺化反应。

Catalyst-Free Singlet Oxygen-Promoted Decarboxylative Amidation of α-Keto Acids with Free Amines.

机构信息

School of Biological and Medical Engineering, Hefei University of Technology, Key Laboratory of Advanced Functional Materials and Devices of Anhui Province , Hefei 230009, P. R. China.

出版信息

Org Lett. 2016 Jul 1;18(13):3114-7. doi: 10.1021/acs.orglett.6b01296. Epub 2016 Jun 15.

DOI:10.1021/acs.orglett.6b01296
PMID:27305073
Abstract

A novel catalyst-free decarboxylative amidation of α-keto acids with amines under mild conditions has been developed. Advantages of the new protocol include avoidance of metal catalysts and high levels of functional group tolerance. In addition, the reaction can be scaled up and shows high chemoselectivity. Preliminary mechanistic studies suggest that singlet oxygen, generated from oxygen under irradiation, is the key promoter for this catalyst-free transformation.

摘要

发展了一种在温和条件下无催化剂的α-酮酸与胺的脱羧酰胺化反应。新反应的优点包括避免使用金属催化剂和对官能团具有高容忍度。此外,该反应可以放大规模,并表现出高的化学选择性。初步的机理研究表明,光照下氧气产生的单线态氧是这种无催化剂转化的关键促进剂。

相似文献

1
Catalyst-Free Singlet Oxygen-Promoted Decarboxylative Amidation of α-Keto Acids with Free Amines.无催化剂的单重态氧促进的α-酮酸与游离胺的脱羧酰胺化反应。
Org Lett. 2016 Jul 1;18(13):3114-7. doi: 10.1021/acs.orglett.6b01296. Epub 2016 Jun 15.
2
Silver-promoted decarboxylative amidation of α-keto acids with amines.银促进的α-酮酸与胺的脱羧酰胺化反应。
Org Biomol Chem. 2016 Oct 25;14(42):9970-9973. doi: 10.1039/c6ob01963c.
3
Direct amidation of aldoses and decarboxylative amidation of alpha-keto acids: an efficient conjugation method for unprotected carbohydrate molecules.醛糖的直接酰胺化和α-酮酸的脱羧酰胺化:一种用于未保护碳水化合物分子的有效共轭方法。
J Org Chem. 2009 Feb 20;74(4):1549-56. doi: 10.1021/jo802338k.
4
Visible-light-mediated decarboxylation/oxidative amidation of α-keto acids with amines under mild reaction conditions using O(2).可见光促进条件下氧气参与的 α-酮酸与胺的脱羧/氧化酰胺化反应。
Angew Chem Int Ed Engl. 2014 Jan 7;53(2):502-6. doi: 10.1002/anie.201308614. Epub 2013 Nov 24.
5
Transition-Metal-Free Synthesis of Ynones via Decarboxylative Alkynylation of α-Keto Acids under Mild Conditions.温和条件下通过α-酮酸的脱羧炔基化反应无过渡金属合成炔酮
J Org Chem. 2015 Sep 18;80(18):9314-20. doi: 10.1021/acs.joc.5b01387. Epub 2015 Aug 28.
6
Direct amidation of carboxylic acids catalyzed by ortho-iodo arylboronic acids: catalyst optimization, scope, and preliminary mechanistic study supporting a peculiar halogen acceleration effect.邻碘芳基硼酸催化的羧酸直接酰胺化反应:催化剂优化、反应范围及支持独特卤原子加速效应的初步机理研究。
J Org Chem. 2012 Oct 5;77(19):8386-400. doi: 10.1021/jo3013258. Epub 2012 Sep 26.
7
9,10-Dicyanoanthracene Catalyzed Decarboxylative Alkynylation of Carboxylic Acids under Visible-Light Irradiation.可见光照射下 9,10-二氰基蒽催化的羧酸脱羧炔基化反应。
J Org Chem. 2016 Dec 16;81(24):12357-12363. doi: 10.1021/acs.joc.6b02385. Epub 2016 Dec 7.
8
Synthesis of Acylhydroquinones through Visible-Light-Mediated Hydroacylation of Quinones with α-Keto Acids.通过可见光介导的醌与α-酮酸的氢酰化反应合成酰基氢醌
J Org Chem. 2024 Feb 2;89(3):1669-1680. doi: 10.1021/acs.joc.3c02361. Epub 2024 Jan 10.
9
Catalyst-Free Synthesis of α-Functionalized 2H-Chromenes in Water: A Tandem Self-Promoted pseudo-Substitution and Decarboxylation Process.水中无催化剂合成α-官能化2H-色烯:串联自促进伪取代和脱羧过程
Chem Asian J. 2019 Sep 2;14(17):2938-2944. doi: 10.1002/asia.201900641. Epub 2019 Aug 7.
10
Sulfonated reduced graphene oxide as a highly efficient catalyst for direct amidation of carboxylic acids with amines using ultrasonic irradiation.磺化还原氧化石墨烯作为一种高效催化剂,用于在超声辐射下羧酸与胺的直接酰胺化反应。
Ultrason Sonochem. 2016 Mar;29:371-9. doi: 10.1016/j.ultsonch.2015.10.009. Epub 2015 Oct 22.

引用本文的文献

1
A mild and scalable one-pot synthesis of N-substituted 2-aminobenzimidazoles via visible light mediated cyclodesulfurization.通过可见光介导的环脱硫反应温和且可扩展地一锅合成N-取代的2-氨基苯并咪唑。
Sci Rep. 2025 Feb 3;15(1):4096. doi: 10.1038/s41598-025-86772-8.
2
Synthesis, characterization, and investigation of photochemical and in vitro properties of novel Zn(II) phthalocyanine.新型锌(II)酞菁的合成、表征及其光化学和体外性质研究
Turk J Chem. 2024 Oct 25;48(6):800-808. doi: 10.55730/1300-0527.3699. eCollection 2024.
3
Visible-light-induced C(sp)-H activation for a C-C bond forming reaction of 3,4-dihydroquinoxalin-2(1)-one with nucleophiles using oxygen with a photoredox catalyst or under catalyst-free conditions.
可见光诱导3,4-二氢喹喔啉-2(1)-酮与亲核试剂发生C-C键形成反应,该反应可使用光氧化还原催化剂或在无催化剂条件下借助氧气进行。
RSC Adv. 2018 May 29;8(35):19580-19584. doi: 10.1039/c8ra03259a. eCollection 2018 May 25.
4
Recent developments in decarboxylative cross-coupling reactions between carboxylic acids and N-H compounds.羧酸与N-H化合物之间脱羧交叉偶联反应的最新进展。
RSC Adv. 2019 Mar 18;9(16):8964-8976. doi: 10.1039/c9ra00929a. eCollection 2019 Mar 15.
5
Palladium-Catalyzed Serendipitous Synthesis of Arylglyoxylic Amides from Arylglyoxylates and ,-Dialkylamides in the Presence of Halopyridines.钯催化下,在卤代吡啶存在的条件下,由芳基乙醛酸酯和N,N-二烷基酰胺意外合成芳基乙醛酰胺。
ACS Omega. 2018 Aug 8;3(8):8787-8793. doi: 10.1021/acsomega.8b00894. eCollection 2018 Aug 31.