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
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
  • [21] Jacques B., 2011, CATALYZED CARBON HET, P119
  • [22] Palladium-Catalyzed Carbo-Heterofunctionalization of Alkenes for the Synthesis of Oxindoles and Spirooxindoles
    Jaegli, Stephanie
    Dufour, Jeremy
    Wei, Hai-long
    Piou, Tiffany
    Duan, Xin-Hua
    Vors, Jean-Pierre
    Neuville, Luc
    Zhu, Jieping
    [J]. ORGANIC LETTERS, 2010, 12 (20) : 4498 - 4501
  • [23] Mechanistic approaches to palladium-catalyzed alkene difunctionalization reactions
    Jensen, Katrina H.
    Sigman, Matthew S.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (22) : 4083 - 4088
  • [24] An efficient and general approach to β-functionalized ketones
    Jiao, Jingliang
    Nguyen, Larry X.
    Patterson, Dennis R.
    Flowers, Robert A., II
    [J]. ORGANIC LETTERS, 2007, 9 (07) : 1323 - 1326
  • [25] Jingliang J., 2007, ORG LETT, V9, P1323
  • [26] Stereoselective Isoxazolidine Synthesis Via Copper-Catalyzed Alkene Aminooxygenation
    Karyakarte, Shuklendu D.
    Smith, Thomas P.
    Chemler, Sherry R.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (17): : 7755 - 7760
  • [27] Copper-Catalyzed One-Pot Trifluoromethylation/Aryl Migration/Desulfonylation and C(sp2)-N Bond Formation of Conjugated Tosyl Amides
    Kong, Wangqing
    Casimiro, Maria
    Merino, Estibaliz
    Nevado, Cristina
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (39) : 14480 - 14483
  • [28] Palladium-catalyzed aerobic oxidative amination of alkenes: Development of intra- and intermolecular Aza-Wacker reactions
    Kotov, Vasily
    Scarborough, Christopher C.
    Stahl, Shannon S.
    [J]. INORGANIC CHEMISTRY, 2007, 46 (06) : 1910 - 1923
  • [29] A convenient way for the conversion of carboxylic esters into 2-substituted allyl halides
    Kulinkovich, OG
    Kozyrkov, YY
    Bekish, AV
    Matiushenkov, EA
    Lysenko, IL
    [J]. SYNTHESIS-STUTTGART, 2005, (10): : 1713 - 1717
  • [30] A novel highly regio- and diastereoselective haloamination of alkenes catalyzed by divalent palladium
    Lei, AW
    Lu, XY
    Liu, GS
    [J]. TETRAHEDRON LETTERS, 2004, 45 (08) : 1785 - 1788