Palladium catalytic system for inhibition of O-arylation type reaction and regioselective direct arylation at C2 of phenols

被引:9
|
作者
Beydoun, Kassem [1 ]
Doucet, Henri [1 ]
机构
[1] Univ Rennes 1 Catalyse & Organometall, CNRS, Inst Sci Chim Rennes, UMR 6226, F-35042 Rennes, France
关键词
ARYL BOND FORMATION; HALIDES; OXYGEN; FUNCTIONALIZATION; HETEROCYCLES; 4-ARYLATION; DERIVATIVES; BENZOFURANS; NAPHTHOLS; SOLVENTS;
D O I
10.1039/c1cy00219h
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The palladium-catalysed arylation of free OH phenol derivatives proceeds regioselectively either at C2 or at OH with a variety of electron-deficient aryl bromides or heteroaryl bromides. The nature of the base was found to be crucial to control the regioselectivity of the reaction. In the presence of potassium acetate, the direct arylation at C2 is favoured; whereas, under the same reaction conditions, the use of potassium carbonate gave selectively the O-arylation type products.
引用
收藏
页码:1243 / 1249
页数:7
相关论文
共 50 条
  • [41] Regioselective Direct C2 Arylation of Indole, Benzothiophene and Benzofuran: Utilization of Reusable Pd NPs and NHC-Pd@MNPs Catalyst for C-H Activation Reaction
    Hegde, Rajeev V.
    Ong, Tiow-Gan
    Ambre, Ram
    Jadhav, Arvind H.
    Patil, Siddappa A.
    Dateer, Ramesh B.
    CATALYSIS LETTERS, 2021, 151 (05) : 1397 - 1405
  • [42] Highly Regioselective Palladium-Catalyzed Direct Arylation of Oxazole at C-2 or C-5 with Aryl Bromides, Chlorides, and Triflates
    Strotman, Neil A.
    Chobanian, Harry R.
    Guo, Yan
    He, Jiafang
    Wilson, Jonathan E.
    ORGANIC LETTERS, 2010, 12 (16) : 3578 - 3581
  • [43] Regioselective C-2 or C-5 Direct Arylation of Pyrroles with Aryl Bromides using a Ligand-Free Palladium Catalyst
    Roger, Julien
    Doucet, Henri
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (11-12) : 1977 - 1990
  • [44] A Palladium/Copper Bimetallic Catalytic System: Dramatic Improvement for Suzuki-Miyaura-Type Direct C-H Arylation of Azoles with Arylboronic Acids
    Liu, Bo
    Qin, Xurong
    Li, Kaizhi
    Li, Xiyu
    Guo, Qiang
    Lan, Jingbo
    You, Jingsong
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (39) : 11836 - 11839
  • [45] Palladium-catalyzed direct C2-arylation of azoles with aromatic triazenes
    Liu, Can
    Wang, Zhiming
    Wang, Lei
    Li, Pinhua
    Zhang, Yicheng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (41) : 9209 - 9216
  • [46] Palladium-Catalyzed Regioselective C-2 Arylation of Benzofurans with N-Acyl Arylhydrazines
    Cao, Jun
    Chen, Zi-Li
    Li, Shu-Min
    Zhu, Gao-Feng
    Yang, Yuan-Yong
    Wang, Cong
    Chen, Wen-Zhang
    Wang, Jian-Ta
    Zhang, Ji-Quan
    Tang, Lei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (22) : 2774 - 2779
  • [47] Orientation effects on C2(5)-C2′(5′) linked bioxazole isomers synthesized via regioselective and sequential C-H arylation
    Guo, Qiang
    Tao, Li
    Liu, Chuanqi
    Zhao, Xiaoyun
    Wan, Danyang
    Zhang, Jincheng
    Ai, Jianping
    Li, Jie
    CHINESE CHEMICAL LETTERS, 2021, 32 (01) : 425 - 428
  • [48] (2-Pyridyl)acetone-Promoted Cu-Catalyzed O-Arylation of Phenols with Aryl Iodides, Bromides, and Chlorides
    Zhang, Qi
    Wang, Deping
    Wang, Xianyang
    Ding, Ke
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (18): : 7187 - 7190
  • [49] Palladium-catalyzed regioselective direct C-H arylation of pyrazolo [3,4-d]pyrimidines
    El Hafi, Mohamed
    Naas, Mohammed
    Loubidi, Mohammed
    Jouha, Jabrane
    Ramli, Youssef
    Mague, Joel T.
    Essassi, El Mokhtar
    Guillaumet, Gerald
    COMPTES RENDUS CHIMIE, 2017, 20 (9-10) : 927 - 933
  • [50] On-Water and Efficient Ullmann-Type O-Arylation Cross Coupling Reaction of Phenols and Aryl Tosylates in the Presence of Fe3O4@Starch-Au as Nanocatalyst
    Mousavi-Mashhadi, Seyed Ali
    Shiri, Ali
    CHEMISTRYSELECT, 2021, 6 (16): : 3941 - 3951