Flexible Gold-Catalyzed Regioselective Oxidative Difunctionalization of Unactivated Alkenes

被引：189
|
作者：
de Haro, Teresa [1 ]
Nevado, Cristina [1 ]
机构：
[1] Univ Zurich, Inst Organ Chem, CH-8006 Zurich, Switzerland
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 04期
关键词：
alkenes; amino alcohols; gold; homogeneous catalysis; oxidation; N-FLUOROBENZENESULFONIMIDE; REDUCTIVE ELIMINATION; BOND FORMATION; C-O; DIAMINATION; AMINOACETOXYLATION; AMINOHYDROXYLATION; NITRILES; AMINOOXYGENATION; DERIVATIVES;
D O I：
10.1002/anie.201005763
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
AuI/AuIII catalytic cycles can trigger three highly regioselective alkene difunctionalization processes that involve the formation of C(sp3)iO, C(sp3)iN, and C(sp3)iC(sp 2) bonds. The reaction can proceed by reductive elimination on the oxidized gold center with complete retention of the configuration or through two subsequent nucleophilic substitution reactions via an aziridine intermediate. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：906 / 910
页数：5
相关论文
共 50 条
  • [21] Gold-catalyzed regioselective oxidation of terminal allenes: formation of α-methanesulfonyloxy methyl ketones
    Luo, Yingdong
    Zhang, Guozhu
    Hwang, Erik S.
    Wilcoxon, Thomas A.
    Zhang, Liming
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 : 596 - 600
  • [22] A Gold-Catalyzed Acid-Assisted Regioselective Cyclization for the Synthesis of Polysubstituted Oxazoles
    Wang, Qian
    Hoffmann, Stephanie
    Schiessl, Jasmin
    Rudolph, Matthias
    Rominger, Frank
    Hashmi, A. Stephen K.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (16) : 2384 - 2388
  • [23] Gold-Catalyzed Intramolecular Oxidative Cross-Coupling of Nonactivated Arenes
    Hopkinson, Matthew N.
    Tessier, Arnaud
    Salisbury, Andrew
    Giuffredi, Guy T.
    Combettes, Lorraine E.
    Gee, Antony D.
    Gouverneur, Veronique
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (16) : 4739 - 4743
  • [24] Gold-Catalyzed 1,2-Diarylation of Alkenes
    Chintawar, Chetan C.
    Yadav, Amit K.
    Patil, Nitin T.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (29) : 11808 - 11813
  • [25] Gold-catalyzed efficient regioselective addition of arenes to allenes
    Skouta, Rachid
    Li, Chao-Jun
    CANADIAN JOURNAL OF CHEMISTRY, 2008, 86 (06) : 616 - 620
  • [26] Regioselective Dihalohydration Reactions of Propargylic Alcohols: Gold-Catalyzed and Noncatalyzed Reactions
    D'Oyley, Jarryl M.
    Aliev, Abil E.
    Sheppard, Tom D.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (40) : 10747 - 10750
  • [27] Efficient Gold(I)-Catalyzed Direct Intramolecular Hydroalkylation of Unactivated Alkenes with α-Ketones
    Xiao, Ya-Ping
    Liu, Xin-Yuan
    Che, Chi-Ming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (21) : 4937 - 4941
  • [28] Gold-catalyzed direct oxidative coupling reactions of non-activated arenes
    Kar, Anirban
    Mangu, Naveenkumar
    Kaiser, Hanns Martin
    Tse, Man Kin
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (04) : 524 - 537
  • [29] An Intermolecular Palladium-Catalyzed Diamination of Unactivated Alkenes
    Iglesias, Alvaro
    Perez, Edwin G.
    Muniz, Kilian
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (44) : 8109 - 8111
  • [30] Palladium-Catalyzed Oxidative Intermolecular Difunctionalization of Terminal Alkenes with Organostannanes and Molecular Oxygen
    Urkalan, Kaveri Balan
    Sigman, Matthew S.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (17) : 3146 - 3149
12345