Palladium(II)-Catalyzed Direct ortho-C-H Acylation of Anilides by Oxidative Cross-Coupling with Aldehydes using tert-Butyl Hydroperoxide as Oxidant

被引：128
作者：
Chan, Chun-Wo [1 ]
Zhou, Zhongyuan [1 ]
Yu, Wing-Yiu [1 ]
机构：
[1] Hong Kong Polytech Univ, State Key Lab Chirosci, Dept Appl Biol & Chem Technol, Kowloon, Hong Kong, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 16期
关键词：
acylation; 2-aminobenzophenones; C?H activation; Friedel-Crafts reaction; palladium; BOND FORMATION; STEREOSELECTIVE-SYNTHESIS; RADICAL REACTIONS; SUGASAWA REACTION; ORTHO-ARYLATION; O BOND; PD; CHEMISTRY; ARENES; SP(2);
D O I：
10.1002/adsc.201100472
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient palladium-catalyzed C?H acylation with aldehydes using tert-butyl hydroperoxide (TBHP) transforms various anilides into synthetically useful 2-aminobenzophenone derivatives under mild conditions (40?degrees C, 3 h). The acylation reaction exhibits excellent regioselectivity and functional group tolerance, and simple aromatic aldehydes, functionalized aliphatic aldehydes and heteroaromatic aldehydes are effective coupling partners. The acylation reaction is probably initiated by a rate-limiting electrophilic C?H cyclopalladation (kH/kD=3.6; ?+=-0.74) to form an arylpalladium complex, followed by acyl radical functionalization.
引用
收藏
页码：2999 / 3006
页数：8
相关论文
共 47 条
  • [21] Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality
    Chen, Xiao
    Engle, Keary M.
    Wang, Dong-Hui
    Yu, Jin-Quan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) : 5094 - 5115
  • [22] Palladium-Catalyzed Direct Ortho-C-H Selenylation of Benzaldehydes Using Benzidine as a Transient Directing Group
    Qiao, Huihao
    Sun, Bing
    Yu, Qinqin
    Huang, Yi-Yong
    Zhou, Yirong
    Zhang, Fang-Lin
    ORGANIC LETTERS, 2019, 21 (17) : 6914 - 6918
  • [23] Kinetic Resolution of Benzylamines via Palladium(II)-Catalyzed C-H Cross-Coupling
    Xiao, Kai-Jiong
    Chu, Ling
    Chen, Gang
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (24) : 7796 - 7800
  • [24] Cobalt (II)-catalyzed direct C3-selective C-H acyloxylation of indoles with tert-butyl peresters
    Zhou, Yuxiang
    Chen, Guojun
    Li, Chenglong
    Liu, Xiaozu
    Liu, Peijun
    SYNTHETIC COMMUNICATIONS, 2018, 48 (22) : 2912 - 2922
  • [25] Oxygen as an oxidant in rhodium(III) catalyzed oxidative C-H/C-H cross-coupling between indoles and oxazoles
    Wang, Yan
    Lan, Jingbo
    SCIENCE CHINA-CHEMISTRY, 2018, 61 (02) : 200 - 205
  • [26] Oxidative Nickel-Air Catalysis in C-H Arylation: Direct Cross-Coupling of Azoles with Arylboronic Acids using Air as Sole Oxidant
    Hachiya, Hitoshi
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    CHEMCATCHEM, 2010, 2 (11) : 1403 - 1406
  • [27] Propargylic C-H activation using a Cu(II) 2-quinoxalinol salen catalyst and tert-butyl hydroperoxide
    Black, Clayton C.
    Gorden, Anne E. V.
    TETRAHEDRON LETTERS, 2018, 59 (09) : 803 - 806
  • [28] Palladium(II)-Catalyzed C-H Activation and C-C Coupling/Cyclization of Benzamidine and Terminal Alkynes Using an Internal Oxidant
    Zhang, Xu
    Xu, Xuefeng
    Wu, Yingke
    Wang, Zhiqiang
    Yu, Lintao
    Zhao, Qiang
    Shi, Fu
    SYNLETT, 2015, 26 (13) : 1885 - 1889
  • [29] Iron(II)-Catalyzed Oxidation of sp3 C-H Bonds Adjacent to a Nitrogen Atom of Unprotected Arylureas with tert-Butyl Hydroperoxide in Water
    Wei, Ying
    Ding, Hongqian
    Lin, Shaoxia
    Liang, Fushun
    ORGANIC LETTERS, 2011, 13 (07) : 1674 - 1677
  • [30] Palladium(II)-catalyzed cross-coupling of simple alkenes with acrylates: a direct approach to 1,3-dienes through C-H activation
    Wen, Zhen-Kang
    Xu, Yun-He
    Loh, Teck-Peng
    CHEMICAL SCIENCE, 2013, 4 (12) : 4520 - 4524
12345