Activation of a C(sp3)?H Bond by a Transient s-Alkylpalladium(II) Complex: Synthesis of Spirooxindoles Through a Palladium-Catalyzed Domino Carbopalladation/C(sp3)?C(sp3) Bond-Forming Process

被引：173
作者：
Piou, Tiffany [2 ]
Neuville, Luc [1 ]
Zhu, Jieping [2 ]
机构：
[1] CNRS, Inst Chim Subst Nat, Lab Int Associe, Ctr Rech Gif, F-91198 Gif Sur Yvette, France
[2] Ecole Polytech Fed Lausanne, EPFL SB ISIC LSPN, BCH 5304, CH-1015 Lausanne, Switzerland
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 46期
基金：
瑞士国家科学基金会;
关键词：
C-H activation; domino reaction; heterocycles; palladium; spirooxindoles; C-H ACTIVATION; C(SP(3))-H BONDS; DIRECT ARYLATION; CYCLIZATION; FUNCTIONALIZATION; CONSTRUCTION; INDOLINES; OXINDOLES; ALKENES; CARBON;
D O I：
10.1002/anie.201206267
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Heck shortens the distance: A method for the palladium-catalyzed activation of a C(sp 3)-H bond by a σ-alkyl Pd II complex generated in-situ from a remote arylhalide function has been developed. This approach allows a novel domino carbopalladation/C(sp 3)-C(sp 3) bond-forming process to provide rapid access to biologically relevant spirooxindoles. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：11561 / 11565
页数：5
相关论文
共 115 条
[91]   Formation of pentacyclic structures by a domino sequence on cyclic enamides [J].
Satyanarayana, Gedu ;
Maichle-Moessmer, Caecilia ;
Maier, Martin E. .
CHEMICAL COMMUNICATIONS, 2009, (12) :1571-1573
[92]   EFFECT OF CONFORMATIONAL CHANGE ON REACTIVITY IN ORGANIC-CHEMISTRY - EVALUATIONS, APPLICATIONS, AND EXTENSIONS OF CURTIN-HAMMETT WINSTEIN-HOLNESS KINETICS [J].
SEEMAN, JI .
CHEMICAL REVIEWS, 1983, 83 (02) :83-134
[93]   Auxiliary-Assisted Palladium-Catalyzed Arylation and Alkylation of sp2 and sp3 Carbon-Hydrogen Bonds [J].
Shabashov, Dmitry ;
Daugulis, Olafs .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) :3965-3972
[94]  
Shi B.-F., 2008, Angew. Chem, V120, P4960
[95]   PdII-catalyzed enantioselective activation of C(sp2)-H and C(sp3)-H bonds using monoprotected amino acids as chiral ligands [J].
Shi, Bing-Feng ;
Maugel, Nathan ;
Zhang, Yang-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (26) :4882-4886
[96]  
Simmons E.M., 2012, Angew. Chem, V124, P3120
[97]   On the Interpretation of Deuterium Kinetic Isotope Effects in C?H Bond Functionalizations by Transition-Metal Complexes [J].
Simmons, Eric M. ;
Hartwig, John F. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (13) :3066-3072
[98]   Catalytic functionalization of unactivated primary C-H bonds directed by an alcohol [J].
Simmons, Eric M. ;
Hartwig, John F. .
NATURE, 2012, 483 (7387) :70-73
[99]   Aerobic Pd-Catalyzed sp3 C-H Olefination: A Route to Both N-Heterocyclic Scaffolds and Alkenes [J].
Stowers, Kara J. ;
Fortner, Kevin C. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (17) :6541-6544
[100]   REARRANGEMENT IN THE PALLADIUM-CATALYZED CYCLIZATION OF ALPHA-SUBSTITUTED N-ACRYLOYL-ORTHO-BROMOANILINES [J].
TERPKO, MO ;
HECK, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (18) :5281-5283
3456789101112