Silver-Catalyzed Tandem Radical Cyclization for the Synthesis of 3,3′-Disubstituted Oxindoles

被引：10
作者：
Li, Yonghong [1 ]
Wang, Junjiao [1 ]
Wei, Xiaohong [1 ]
Yang, Shangdong [1 ]
机构：
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 35卷 / 03期
基金：
中国国家自然科学基金;
关键词：
silver-catalyzed; radical tandem cyclization; C-H functionalization; carbonyl-containing 3,3 '-disubstituted oxindoles; N-ARYL ACRYLAMIDES; ACTIVATED ALKENES; H ACTIVATION; BOND; DIAMINATION; CASCADE; FUNCTIONALIZATION; AMINOOXYGENATION; EFFICIENT; CARBOCYCLIZATION;
D O I：
10.6023/cjoc201412030
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new silver-catalyzed oxidative ring opening of cyclopropanols to functionalize alkenes of N-arylacrylamides leading to 3,3'-disubstituted oxindoles has been developed. This reaction is proposed to proceed through oxidative radical ring-opening and C-H functionalization cascade process under the mild reaction conditions with good functional groups tolerance.
引用
收藏
页码：638 / 646
页数：9
相关论文
共 91 条
  • [1] Palladium-catalyzed ring-forming aminoacetoxylation of alkenes
    Alexanian, EJ
    Lee, C
    Sorensen, EJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (21) : 7690 - 7691
  • [2] Palladium-Catalyzed Tandem Diperoxidation/C-H Activation Resulting in Diperoxy-oxindole in Air
    An, Guanghui
    Zhou, Wei
    Zhang, Guangqian
    Sun, Hao
    Han, Jianlin
    Pan, Yi
    [J]. ORGANIC LETTERS, 2010, 12 (20) : 4482 - 4485
  • [3] [Anonymous], 2009, ANGEW CHEM INT ED
  • [4] BARLUENGA J, 1987, SYNTHESIS-STUTTGART, P584
  • [5] Design and formation of a large tetrahedral cluster using 1,1′-binaphthyl ligands
    Biros, Shannon M.
    Yeh, Robert M.
    Raymond, Kenneth N.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (32) : 6062 - 6064
  • [6] Modulating the Ground- and Excited-State Oxidation Potentials of Diaminonaphthalene by Sequential N-Methylation
    Campbell, Neil P.
    Finch, Amethist S.
    Rokita, Steven E.
    [J]. CHEMPHYSCHEM, 2010, 11 (08) : 1768 - 1773
  • [7] Palladium-Catalyzed Intramolecular Diamination of Acrylic Esters Using Sulfamates as Nitrogen Source
    Chavez, Patricia
    Kirsch, Jonathan
    Streuff, Jan
    Muniz, Kilian
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (04) : 1922 - 1930
  • [8] The enantioselective intramolecular aminative functionalization of unactivated alkenes, dienes, allenes and alkynes for the synthesis of chiral nitrogen heterocycles
    Chemler, Sherry R.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (15) : 3009 - 3019
  • [9] Generation of β-keto radicals from cyclopropanols catalyzed by AgNO3
    Chiba, S
    Cao, ZY
    El Bialy, SAA
    Narasaka, K
    [J]. CHEMISTRY LETTERS, 2006, 35 (01) : 18 - 19
  • [10] Complementary Regioselectivity in the Cu(I)-Catalyzed Diamination of Conjugated Dienes To Form Cyclic Sulfamides
    Cornwall, Richard G.
    Zhao, Baoguo
    Shi, Yian
    [J]. ORGANIC LETTERS, 2011, 13 (03) : 434 - 437
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