以水和氧气作为氧源，铜催化合成α-酮酰胺。
Copper-catalyzed synthesis of α-ketoamides using water and dioxygen as the oxygen source.
作者信息
Xiao Yuanyuan, Yi Zijuan, Yu Xianyong, Xiao Fang
机构信息
Department of Health Toxicology, Xiangya School of Public Health, Central South University Changsha 410078 PR China
School of Chemistry and Chemical Engineering, Hunan University of Science and Technology Xiangtan 411201 China.
出版信息
RSC Adv. 2020 Aug 6;10(49):29114-29118. doi: 10.1039/d0ra05921h. eCollection 2020 Aug 5.
Abstract
The reaction employing HO and O as the co-oxygen source in the catalytic synthesis of α-ketoamides is described. This copper-catalyzed reaction is carried out in a tandem manner constituted by the hydroamination of alkyne, hydration of vinyl-Cu complex and subsequent oxidation. Isotope labeling and radical capture experiments reveal that the oxygen atom of α-ketone at α-ketoamides derives from O and the oxygen atom of amide group originates from HO.
摘要
描述了在催化合成α-酮酰胺中使用HO和O作为共氧源的反应。这种铜催化反应以串联方式进行，由炔烃的氢胺化、乙烯基铜配合物的水合以及随后的氧化组成。同位素标记和自由基捕获实验表明，α-酮酰胺中α-酮的氧原子来自O，酰胺基团的氧原子来自HO。
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本文引用的文献
1
C-H Imidation and Dual C-H Bond Aminobromination of Five-Membered Heterocycles.
J Org Chem. 2020 Jan 17;85(2):1001-1008. doi: 10.1021/acs.joc.9b02941. Epub 2020 Jan 3.
2
Visible-Light-Enabled Construction of Thiocarbamates from Isocyanides, Thiols, and Water at Room Temperature.
Org Lett. 2018 Sep 7;20(17):5291-5295. doi: 10.1021/acs.orglett.8b02231. Epub 2018 Aug 21.
3
Synthesis of aminouracil-tethered tri-substituted methanes in water by iodine-catalyzed multicomponent reactions.
Mol Divers. 2019 Feb;23(1):205-213. doi: 10.1007/s11030-018-9862-z. Epub 2018 Aug 14.
4
Multicomponent Synthesis of Tetrahydroisoquinolines.
Org Lett. 2018 Jun 15;20(12):3460-3464. doi: 10.1021/acs.orglett.8b01159. Epub 2018 May 29.
5
Heteropolyacid-Containing Ionic Liquid-Catalyzed Multicomponent Synthesis of Bridgehead Nitrogen Heterocycles: Mechanisms and Mitochondrial Staining.
J Org Chem. 2018 Apr 6;83(7):4044-4053. doi: 10.1021/acs.joc.8b00472. Epub 2018 Mar 29.
6
Metal-Free Geminal Difunctionalization of Diazocarbonyl Compounds: A One-Pot Multicomponent Strategy for the Construction of α,β-Diamino Carbonyl Derivatives.
Chemistry. 2018 Apr 3;24(19):4805-4809. doi: 10.1002/chem.201800555. Epub 2018 Mar 13.
7
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Org Biomol Chem. 2012 Dec 14;10(46):9237-42. doi: 10.1039/c2ob26586a. Epub 2012 Oct 26.
8
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Angew Chem Int Ed Engl. 2011 Nov 18;50(47):11088-92. doi: 10.1002/anie.201105285. Epub 2011 Sep 14.
9
Zinc chloride promoted formal oxidative coupling of aromatic aldehydes and isocyanides to alpha-ketoamides.
J Org Chem. 2010 Apr 16;75(8):2748-51. doi: 10.1021/jo100302y.
10
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Chem Commun (Camb). 2010 Jan 7;46(1):130-2. doi: 10.1039/b917958e. Epub 2009 Nov 3.
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