Photocatalytic α-Oxyamination of Stable Enolates, Silyl Enol Ethers, and 2-Oxoalkane Phosphonic Esters

被引：35
|
作者：
Schroll, Peter [1 ]
Koenig, Burkhard [1 ]
机构：
[1] Univ Regensburg, Inst Organ Chem, D-93053 Regensburg, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 02期
关键词：
Photooxidation; Photocatalysis; Radicals; Flow catalysis; Microreactors; LIGHT-DRIVEN OXIDATION; VISIBLE-LIGHT; AEROBIC OXIDATION; 1,3-DICARBONYL COMPOUNDS; PHOTOREDOX CATALYSIS; ALCOHOLS; ALDEHYDES; EFFICIENT; RADICALS; ALKENES;
D O I：
10.1002/ejoc.201403433
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Fast alpha-oxyamination of stable enolates, silyl enol ethers, and in situ deprotonated dialkyl 2-oxoalkane phosphonates and diphenyl-2-oxoalkyl phosphine oxides was performed in the presence of [Ru(bpy)(3)](2+) (bpy = 2,2'-bipyridyl) as a photocatalyst, 2,2,6,6-tetramethylpiperidine nitroxide (TEMPO), and visible light. The key step was the light-induced one-electron oxidation of TEMPO into the 2,2,6,6-tetramethylpiperidine1- oxoammonium ion, which was nucleophilically attacked to yield alpha-functionalized carbonyl compounds. The reaction time was significantly reduced by the use of the microreactor flow technique.
引用
收藏
页码：309 / 313
页数：5
相关论文
共 14 条
  • [1] Rhodium-Catalyzed β-Dehydroborylation of Silyl Enol Ethers: Access to Highly Functionalized Enolates
    Li, Jie
    Zhao, Pei
    Li, Ruoling
    Yang, Wen
    Zhao, Wanxiang
    ORGANIC LETTERS, 2021, 23 (24) : 9580 - 9585
  • [2] Photoredox Reaction of 2-Mercaptothiazolinium Salts with Silyl Enol Ethers
    Zemtsov, Artem A.
    Ashirbaev, Salavat S.
    Levin, Vitalij V.
    Kokorekin, Vladimir A.
    Korlyukov, Alexander A.
    Dilman, Alexander D.
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (23): : 15745 - 15753
  • [3] Visible-Light-Promoted Oxidative [4+2] Cycloadditions of Aryl Silyl Enol Ethers
    Yang, Bo
    Lu, Zhan
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16): : 7288 - 7300
  • [4] Visible-Light-Induced Photocatalysis of 1,1,1-Trifluoro-2-iodoethane with Alkylalkenes and Silyl Enol Ethers
    Huang, Meiwei
    Li, Lun
    Zhao, Zhi-Gang
    Chen, Qing-Yun
    Guo, Yong
    SYNTHESIS-STUTTGART, 2015, 47 (24): : 3891 - 3900
  • [5] Copper-Catalyzed Enantioselective Mukaiyama Aldol Reaction of Silyl Enol Ethers with Isatin-Derived Oxindolyl β,γ-Unsaturated α-Keto Esters
    Lu, Wenjing
    Li, Jindong
    Lu, Yangmian
    Zha, Zhenggen
    Wang, Zhiyong
    CHEMISTRYSELECT, 2021, 6 (03): : 410 - 414
  • [6] Iron-Catalyzed Highly Enantioselective Addition of Silyl Enol Ethers to α,β-Unsaturated 2-Acyl Imidazoles
    Wei, Jinhu
    Huang, Jie-Sheng
    Che, Chi-Ming
    ORGANIC LETTERS, 2021, 23 (17) : 6993 - 6997
  • [7] Synthesis of Tetrasubstituted Furans by Using Photoredox-Catalyzed Coupling of 2-Bromo-1,3-dicarbonyl Compounds with Silyl Enol Ethers
    Han, Yue-Yue
    Jiao, Yan-Yan
    Ren, Daan
    Hu, Zhentao
    Shen, Sheng
    Yu, Shouyun
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (04) : 414 - 417
  • [8] A Chiral N,N′-Dioxide-ZnII Complex Catalyzes the Enantioselective [2+2] Cycloaddition of Alkynones with Cyclic Enol Silyl Ethers
    Kang, Tengfei
    Ge, Shulin
    Lin, Lili
    Lu, Yan
    Liu, Xiaohua
    Feng, Xiaoming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (18) : 5541 - 5544
  • [9] Enantioselective MukaiyamaMichael Reaction of Silyl Enol Ethers to 2-Enoylpyridine N-Oxides Catalyzed by Copper- Bis(oxazoline) Complex
    George, Jimil
    Reddy, Basi V. Subba
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (2-3) : 383 - 388
  • [10] Sunlight-driven synthesis of γ-diketones via oxidative coupling of enamines with silyl enol ethers catalyzed by [Ru(bpy)3]2+
    Yasu, Yusuke
    Koike, Takashi
    Akita, Munetaka
    CHEMICAL COMMUNICATIONS, 2012, 48 (43) : 5355 - 5357
12