Palladium-Catalyzed β-Arylation of Silyl Ketene Acetals and Application to the Synthesis of Benzo-Fused δ-Lactones

被引：27
|
作者：
Aspin, Sam [1 ]
Lopez-Suarez, Laura [1 ]
Larini, Paolo [1 ]
Goutierre, Anne-Sophie [1 ]
Jazzar, Rodolphe [1 ]
Baudoin, Olivier [1 ]
机构：
[1] Univ Lyon 1, Inst Chim & Biochim Mol & Supramol, CNRS UMR 5246, CPE Lyon, F-69622 Villeurbanne, France
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 19期
关键词：
C-H BONDS; ALPHA-ARYLATION; COUPLING REACTIONS; KETO-ESTERS; METAL; FUNCTIONALIZATION; EFFICIENT; SP(2); ACIDS;
D O I：
10.1021/ol402398s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Silyl ketene acetals are shown to be competent nucleophiles in Pd-catalyzed migrative C(sp(3))-H arylations. Compared to the parent ester lithium enolates, they possess decreased reactivity but enhanced chemoselectivity. This behavior was exploited through the synthesis of valuable benzo-fused delta-lactones such as 1-isochromanones and dihydrocoumarins.
引用
收藏
页码：5056 / 5059
页数：4
相关论文
共 50 条
  • [1] Palladium-Catalyzed γ-Arylation of α,β-Unsaturated Esters from Silyl Ketene Acetals
    Huang, David S.
    Hartwig, John F.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (33) : 5757 - 5761
  • [2] Synthesis of α-Heteroaryl Propionic Esters by Palladium-Catalyzed α-Heteroarylation of Silyl Ketene Acetals
    Li, Bowen
    Luo, Bangke
    Blakemore, Caroline A.
    Smith, Aaron C.
    Widlicka, Daniel W.
    Berritt, Simon
    Tang, Wenjun
    ORGANIC LETTERS, 2021, 23 (16) : 6439 - 6443
  • [3] PALLADIUM-CATALYZED ARYLATION OF ALPHA-METHOXYKETENE METHYL SILYL ACETALS
    SAKAMOTO, T
    KONDO, Y
    MASUMOTO, K
    YAMANAKA, H
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (03): : 235 - 236
  • [4] Synthesis of benzo-fused five- and six-membered heterocycles by palladium-catalyzed cyclocarbonylation
    Troisi, Luigino
    Granito, Catia
    Perrone, Serena
    Rosato, Francesca
    TETRAHEDRON LETTERS, 2011, 52 (33) : 4330 - 4332
  • [5] Palladium-Catalyzed Amination and Amidation of Benzo-Fused Bromine-Containing Heterocycles
    A. G. Sergeev
    G. A. Artamkina
    V. S. Velezheva
    I. N. Fedorova
    I. P. Beletskaya
    Russian Journal of Organic Chemistry, 2005, 41 : 860 - 874
  • [6] Palladium-catalyzed amination and amidation of benzo-fused bromine-containing heterocycles
    Sergeev, AG
    Artamkina, GA
    Velezheva, VS
    Fedorova, IN
    Beletskaya, IP
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 41 (06) : 860 - 874
  • [7] PALLADIUM-CATALYZED ARYLATION OF UNSATURATED ACETALS AND KETALS
    ZEBOVITZ, TC
    HECK, RF
    JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (24): : 3907 - 3909
  • [8] Synthesis of neutral π-allylpalladium complexes having bisnitrogen ligands and palladium-catalyzed cyclopropanation of ketene silyl acetals with allylic acetates
    Satake, A
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2000, 58 (08) : 736 - 744
  • [9] Palladium-catalyzed intramolecular O-arylation of enolates:: Application to benzo[b]furan synthesis
    Willis, MC
    Taylor, D
    Gillmore, AT
    ORGANIC LETTERS, 2004, 6 (25) : 4755 - 4757
  • [10] Synthesis of Benzo-fused Heterocycles by Intramolecular α-Arylation of Ketone Enolate Anions
    Guastavino, Javier F.
    Rossi, Roberto A.
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01): : 460 - 472
12345