Palladium-Catalyzed Domino Dehydrogenation/Heck-Type Reactions of Carbonyl Compounds

被引：27
|
作者：
Le Bras, Jean [1 ]
Muzart, Jacques [1 ]
机构：
[1] Univ Reims, CNRS, Inst Chim Mol Reims, UMR 7312, BP 1039, F-51687 Reims 2, France
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 13期
基金：
美国国家科学基金会;
关键词：
carbonyl compounds; C-H bond activation; dehydrogenation; domino reaction; Heck reaction; palladium; BETA-KETO-ESTERS; INTRAMOLECULAR HECK REACTION; AUTO-TANDEM CATALYSIS; C-H OLEFINATION; EFFICIENT SYNTHESIS; MOLECULAR-OXYGEN; DIRECT ARYLATION; ALPHA-ARYLATION; ARYL HALIDES; DECARBOXYLATIVE PALLADATION;
D O I：
10.1002/adsc.201800258
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
This review covers those domino reactions that involve, at least, both palladium-catalyzed dehydrogenation of carbonyl compounds and Heck-type reactions. While the former occurs under Pd(II) catalysis, a Pd(0) or Pd(II) catalyst is required for the latter, depending on the nature of the (hetero)arylating agent, ArX or ArH, respectively. Regeneration of the Pd(II) species is assumed to proceed by either an oxidant or the aryl halide. Proposed mechanisms are described with, in some cases, personal comments.
引用
收藏
页码：2411 / 2428
页数：18
相关论文
共 50 条
  • [1] Palladium-Catalyzed Heck-Type Reactions of Alkyl Iodides
    Bloome, Kayla S.
    McMahen, Rebecca L.
    Alexanian, Erik J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (50) : 20146 - 20148
  • [2] Palladium-Catalyzed Carbonylative Heck-Type Reactions of Alkyl Iodides
    Bloome, Kayla S.
    Alexanian, Erik J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (37) : 12823 - 12825
  • [3] Palladium-catalyzed intermolecular Heck-type reactions with alkyl iodides
    McMahon, Caitlin
    Alexanian, Erik
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [4] Palladium-Catalyzed Intermolecular Heck-Type Reaction of Epoxides
    Teng, Shenghan
    Tessensohn, Malcolm E.
    Webster, Richard D.
    Zhou, Jianrong Steve
    ACS CATALYSIS, 2018, 8 (08): : 7439 - 7444
  • [5] Palladium-catalyzed heck-type arylation of acrylate with diaryliodonium salts
    Li, Jian
    Liu, Li
    Zhou, Yun-yao
    Xu, Sai-nan
    RSC ADVANCES, 2012, 2 (08) : 3207 - 3209
  • [6] Palladium-Catalyzed Heck-Type Reactions of Allylic Esters with Arylboronic Acids or Potassium Aryltrifluoroborates
    Yao, Bo
    Liu, Yan
    Wang, Meng-Ke
    Li, Jin-Heng
    Tang, Ri-Yuan
    Zhang, Xing-Guo
    Deng, Chen-Liang
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (06) : 1069 - 1076
  • [7] Chelating N-heterocyclic carbene ligands in palladium-catalyzed Heck-type reactions
    Herrmann, WA
    Reisinger, CP
    Spiegler, M
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 557 (01) : 93 - 96
  • [8] Synthetic Strategy: Palladium-Catalyzed Dehydrogenation of Carbonyl Compounds
    Hirao, Toshikazu
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (04): : 1687 - 1692
  • [9] Bipyridine-Modulated Palladium-catalyzed Oxidative Heck-type Reactions of Arylboronic Acids with Olefins
    Hsu, Chien-Ming
    Li, Chih-Bin
    Sun, Chia-Hsing
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2009, 56 (05) : 873 - 880
  • [10] Palladium-catalyzed Heck-type reaction of secondary trifluoromethylated alkyl bromides
    Fan, Tao
    Meng, Wei-Dong
    Zhang, Xingang
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 : 2610 - 2616
12345