Palladium-Catalyzed Direct Arylation-Based Domino Synthesis of Annulated N-Heterocycles Using Alkenyl or (Hetero)Aryl 1,2-Dihalides

被引：66
|
作者：
Ackermann, Lutz [1 ]
Althammer, Andreas [1 ]
Mayer, Peter [2 ]
机构：
[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
[2] Univ Munich, Dept Chem, D-81377 Munich, Germany
来源：
SYNTHESIS-STUTTGART | 2009年 / 20期
关键词：
arylation; catalysis; heterocycles; palladium; sequential reaction; H BOND ACTIVATION; ONE-POT SYNTHESIS; METAL-DIENE COMPLEXES; C-H; ORGANIC-SYNTHESIS; REACTION SEQUENCE; ROOM-TEMPERATURE; ARYL CHLORIDES; CONSECUTIVE AMINATION; SELECTIVE ARYLATION;
D O I：
10.1055/s-0029-1216977
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A palladium-catalyzed reaction sequence consisting of an intermolecular amination and an intramolecular direct arylation enabled highly regioselective syntheses of functionalized indoles or carbazoles and proved to be amenable to the use of inexpensive 1,2-dichloroarenes as electrophiles.
引用
收藏
页码：3493 / 3503
页数：11
相关论文
共 36 条
  • [1] Palladium-catalyzed domino N-benzylation/C-H arylation approach to the synthesis of fused N-heterocycles
    Laha, Joydev K.
    Singh, Swati
    Dayal, Neetu
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
  • [2] Palladium-Catalyzed Domino Direct Arylation/N-Arylation: Convenient Synthesis of Phenanthridines
    Candito, David A.
    Lautens, Mark
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (36) : 6713 - 6716
  • [3] Domino N-H/C-H bond activation: Palladium-catalyzed synthesis of annulated heterocycles using dichloro(hetero)arenes
    Ackermann, Lutz
    Althammer, Andreas
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) : 1627 - 1629
  • [4] Synthesis of pyrrolo[1,2-f]phenanthridine-annulated polycyclic heterocycles from palladium-catalyzed intramolecular direct arylation reaction
    Roy, Brindaban
    De, Rajendra Narayan
    Hazra, Somjit
    [J]. MONATSHEFTE FUR CHEMIE, 2012, 143 (01): : 119 - 125
  • [5] Synthesis of pyrrolo[1,2-f]phenanthridine-annulated polycyclic heterocycles from palladium-catalyzed intramolecular direct arylation reaction
    Brindaban Roy
    Rajendra Narayan De
    Somjit Hazra
    [J]. Monatshefte für Chemie - Chemical Monthly, 2012, 143 : 119 - 125
  • [6] Formal Synthesis of Nitidine and Nk109 via Palladium-Catalyzed Domino Direct Arylation/N-Arylation of Aryl Triflates
    Blanchot, Mathieu
    Candito, David A.
    Larnaud, Florent
    Lautens, Mark
    [J]. ORGANIC LETTERS, 2011, 13 (06) : 1486 - 1489
  • [7] Synthesis of phenazines by palladium-catalyzed N-arylation of 1,2-diamino(hetero)arenes with 1,2-dihalo(hetero) arenes
    Laha, Joydev K.
    Satyanarayana, K. S. T.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
  • [8] Palladium-Catalyzed Carbonylative Synthesis of N-Heterocycles from 1-Chloro-2-fluorobenzenes
    Yuan, Yang
    Wu, Xiao-Feng
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (11) : 2172 - 2175
  • [9] ORGN 301-Synthesis of benzannulated N-heterocycles by a domino palladium-catalyzed C-C/C-N coupling
    Thansandote, Praew
    Rudolph, Alena
    Raemy, Manuel
    Lautens, Mark
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
  • [10] Regioselective Synthesis of 1,2-and 1,4-Dihydroquinolines by Palladium-Catalyzed Intramolecular N-Arylation
    Park, Kyeong-Yong
    Lee, Jinyong
    Park, Seong Jun
    Heo, Jung-Nyoung
    Lim, Hwan Jung
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (18) : 3917 - 3926
1234