Platinum-Catalyzed C-H Arylation of Simple Arenes

被引：109
|
作者：
Wagner, Anna M. [1 ]
Hickman, Amanda J. [1 ]
Sanford, Melanie S. [1 ]
机构：
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 42期
关键词：
SIGMA-ARYL COMPLEXES; BOND FUNCTIONALIZATION; AROMATIC-COMPOUNDS; REDUCTIVE ELIMINATION; SITE-SELECTIVITY; ACTIVATION; NAPHTHALENE; BENZENE; PALLADIUM(IV); CONSTRUCTION;
D O I：
10.1021/ja408112j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
This report describes the Na2PtCl4 catalyzed C-H arylation of arene substrates with diaryliodonium salts. The site selectivity of these reactions is predominantly controlled by steric factors. Remarkably, Na2PtCl4-catalyzed naphthalene arylation proceeds with opposite site selectivity compared to that obtained with Na2PtCl4 as the catalyst. Preliminary mechanistic studies provide evidence for a Pt-II/Pt-IV catalytic cycle involving rate-limiting C-C bond-forming reductive elimination.
引用
收藏
页码：15710 / 15713
页数：4
相关论文
共 50 条
  • [1] Platinum-catalyzed C-H arylation of simple arenes
    Sanford, M.S. (mssanfor@umich.edu), 1600, American Chemical Society (135):
  • [2] Heterogeneous Platinum-Catalyzed C-H Perfluoroalkylation of Arenes and Heteroarenes
    He, Lin
    Natte, Kishore
    Rabeah, Jabor
    Taeschler, Christoph
    Neumann, Helfried
    Brueckner, Angelika
    Beller, Matthias
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (14) : 4320 - 4324
  • [3] C-H Functionalization at Sterically Congested Positions by the Platinum-Catalyzed Borylation of Arenes
    Furukawa, Takayuki
    Tobisu, Mamoru
    Chatani, Naoto
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (38) : 12211 - 12214
  • [4] Platinum-Catalyzed C-H Functionalization
    Labinger, Jay A.
    CHEMICAL REVIEWS, 2017, 117 (13) : 8483 - 8496
  • [5] Controlling site-selectivity in platinum-catalyzed direct C-H arylation reactions
    Wagner, Anna M.
    Hickman, Amanda J.
    Sanford, Melanie S.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [6] Palladium-Catalyzed Direct C-H Arylation of Enamides with Simple Arenes
    Pankajakshan, Sreekumar
    Xu, Yun-He
    Cheng, Jun Kee
    Low, Man Ting
    Loh, Teck-Peng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (23) : 5701 - 5705
  • [7] Palladium-catalyzed Direct C-H Bond Arylation of Simple Arenes with Aryltrimethylsilanes
    Funaki, Kenji
    Kawai, Hiroshi
    Sato, Tetsuo
    Oi, Shuichi
    CHEMISTRY LETTERS, 2011, 40 (09) : 1050 - 1052
  • [8] Platinum-Catalyzed Allylic C-H Alkylation with Malononitriles
    Fan, Lian-Feng
    Xie, Pei-Pei
    Wang, Pu-Sheng
    Hong, Xin
    Gong, Liu-Zhu
    CCS CHEMISTRY, 2022, 4 (04): : 1366 - 1375
  • [9] Rhodium-Catalyzed C-H Bond Arylation of Arenes
    Bouffard, Jean
    Itami, Kenichiro
    C-H ACTIVATION, 2010, 292 : 231 - 280
  • [10] Direct C-H arylation of simple arenes: Ligand effect and mechanism
    Hong, Soon Hyeok
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
12345