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
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
  • [21] Palladium-catalyzed reductive Heck-type vinylative dearomatization of unfunctionalized halonaphthalene derivatives
    Dou, Yingchao
    Yang, Liting
    Zhang, Lu
    Zhang, Panke
    Li, Heng
    Yang, Guanyu
    RSC ADVANCES, 2016, 6 (102) : 100632 - 100635
  • [22] Palladium-Catalyzed Oxidative Heck-Type Allylation of β,β-Disubstituted Enones with Allyl Carbonates
    Jin, Weiwei
    Yang, Qin
    Wu, Ping
    Chen, Jiping
    Yu, Zhengkun
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (09) : 2097 - 2102
  • [23] Palladium-Catalyzed Desulfitative Heck-Type Reaction of Aryl Sulfinic Acids with Alkenes
    Wang, Guan-Wu
    Miao, Tao
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (21) : 5787 - 5790
  • [24] Palladium-catalyzed Heck-type reaction of oximes with allylic alcohols: synthesis of pyridines and azafluorenones
    Zheng, Meifang
    Chen, Pengquan
    Wu, Wanqing
    Jiang, Huanfeng
    CHEMICAL COMMUNICATIONS, 2016, 52 (01) : 84 - 87
  • [25] Palladium-Catalyzed Heck-Type Coupling of Allyl Esters: β-Hydride versus β-Acetoxy Elimination
    Pan, Delin
    Jiao, Ning
    SYNLETT, 2010, (11) : 1577 - 1588
  • [26] Palladium-catalyzed cascade Heck-type cyclization and reductive aminocarbonylation for the synthesis of functionalized amides
    Ren-Rui Xu
    Wen, Dan
    Qi, Xinxin
    Xiao-Feng Wu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (13) : 2605 - 2608
  • [27] Palladium catalyzed Heck-type Reactions using haloalkenes in place of alkenes in reactions with organic iodides
    Dieck, HA
    Perry, TM
    Xia, P
    Harting, BP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U396 - U396
  • [28] A General Synthesis of Fluoroalkylated Alkenes by Palladium-Catalyzed Heck-Type Reaction of Fluoroalkyl Bromides
    Feng, Zhang
    Min, Qiao-Qiao
    Zhao, Hai-Yang
    Gu, Ji-Wei
    Zhang, Xingang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (04) : 1270 - 1274
  • [29] Phosphine Oxide-Directed Palladium-Catalyzed Heck-Type Functionalization of o-Carboranes
    Lian, Lingxiang
    Yin, Jingyi
    Lin, Caixia
    Ye, Keyin
    Yuan, Yaofeng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (08) : 3249 - 3255
  • [30] Palladium-catalyzed α-vinylation of carbonyl compounds
    Huang, Jinkun
    Bunel, Emilio
    Faul, Margaret M.
    ORGANIC LETTERS, 2007, 9 (21) : 4343 - 4346