Preparation of benzolactams by Pd(OAc)2-catalyzed direct aromatic carbonylation

被引:272
|
作者
Orito, K [1 ]
Horibata, A [1 ]
Nakamura, T [1 ]
Ushito, H [1 ]
Nagasaki, H [1 ]
Yuguchi, M [1 ]
Yamashita, S [1 ]
Tokuda, M [1 ]
机构
[1] Hokkaido Univ, Grad Sch Engn, Div Mol Chem, Organ Synth Lab, Sapporo, Hokkaido 0608628, Japan
关键词
D O I
10.1021/ja045342+
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We developed a new method for Pd(II)-catalyzed direct aromatic carbonylation in a phosphine-free catalytic system using Pd(OAc)2 and Cu(OAc)2 in an atmosphere of CO gas containing air. The carbonylation proceeded with ortho-palladation, inducing a remarkable site selectivity to afford a variety of five- or six-membered benzolactams from secondary ω-arylalkylamines, such as N-alkylbenzylamines or N-alkylphenethylamines. Copyright © 2004 American Chemical Society.
引用
收藏
页码:14342 / 14343
页数:2
相关论文
共 50 条
  • [31] DFT study on the mechanism of Pd(OAc)2-catalyzed hydrothiolation of alkenes bearing heteroatoms with benzenethiol
    Ji, Cai-hong
    Zhang, Xing-hui
    STRUCTURAL CHEMISTRY, 2016, 27 (03) : 919 - 926
  • [32] Microwave assisted Pd(OAc)2-catalyzed chemoselective reduction of aryl α,ß-unsaturated esters with triethylsilane
    Kumar, Yogesh
    Yadav, Renuka
    Sinha, Anshu Kumar
    Rawat, Pooja
    Rao, Gyandshwar Kumar
    Srivastava, Chandra Mohan
    Jangid, Nirmala Kumari
    Srivastava, Anamika
    Srivastava, Manish
    Rawat, Varun
    IRANIAN JOURNAL OF CATALYSIS, 2020, 10 (03): : 203 - 208
  • [33] An Efficient Protocol for a Pd(OAc)2-Catalyzed Ligand-Free Suzuki Reaction in Toluene
    Liu Ning
    Liu Chun
    Jin Zilin
    CHINESE JOURNAL OF CATALYSIS, 2010, 31 (11) : 1316 - 1320
  • [34] Pd(OAc)2-Catalyzed Desulfinative Cross-Coupling of Sodium Sulfinates with β-Bromostyrenes: Synthesis of Tamoxifen
    Chang, Meng-Yang
    Cheng, Yu-Chieh
    Sun, Pei-Pei
    SYNTHESIS-STUTTGART, 2017, 49 (11): : 2411 - 2422
  • [35] Divergent Synthesis of Imidazoles and Quinazolines via Pd(OAc)2-Catalyzed Annulation of N-Allylamidines
    Xu, Li
    Li, Hongxian
    Liao, Ziyang
    Lou, Kaiyan
    Xie, Hexin
    Li, Hao
    Wang, Wei
    ORGANIC LETTERS, 2015, 17 (14) : 3434 - 3437
  • [36] Pd(OAc)2-Catalyzed Ligand-Free Suzuki Reaction in Ethylene Glycol at Room Temperature
    Liu Chun
    Han Na
    Yuan Hao
    He Xiaoyu
    Jin Zilin
    CHINESE JOURNAL OF CATALYSIS, 2011, 32 (07) : 1204 - 1207
  • [37] Pd(OAc)2-Catalyzed Approach to Phenanthridin-6(5H)-one Skeletons
    Li, Ye
    Wang, Dong-Wei
    Liu, Jian-Quan
    Wang, Xiang-Shan
    ORGANIC LETTERS, 2025, 27 (02) : 577 - 582
  • [38] Factors Influencing the Chemoselectivity of Pd(OAc)2-Catalyzed Cyclization Reactions Involving 1,6-Enynes as a Substrate and PhI(OAc)2 as a Reagent
    Shiri, Farshad
    Ariafard, Alireza
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (28)
  • [39] Pd(OAc)2-catalyzed room temperature homocoupling reaction of arylboronic acids under air without ligand
    Xu, Zhou
    Mao, Jincheng
    Zhang, Yawen
    CATALYSIS COMMUNICATIONS, 2008, 9 (01) : 97 - 100
  • [40] Pd(OAc)2-catalyzed C-H activation of indoles: a facile synthesis of 3-cyanoindoles
    Reddy, B. V. Subba
    Begum, Zubeda
    Reddy, Y. Jayasudhan
    Yadav, J. S.
    TETRAHEDRON LETTERS, 2010, 51 (25) : 3334 - 3336