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
  • [31] Oxidative Palladium(II)-Catalyzed Dehydrogenative CH/CH Cross-Coupling of 2,3-Substituted Indolines with Arenes at the C7 Position
    Jiao, Lin-Yu
    Oestreich, Martin
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (33) : 10845 - 10848
  • [32] Palladium-Catalyzed Direct C(sp2)-H ortho-Arylation of Anilides Using 2-Aminophenylpyrazole as the Directing Group
    Shen, Yuning
    Lee, Wan-Chen Cindy
    Gutierrez, David A.
    Li, Jie Jack
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (21) : 11620 - 11625
  • [33] Copper-catalyzed cross-dehydrogenative coupling of N-arylacrylamides with chloroform using tert-butyl peroxybenzoate as oxidant for the synthesis of trichloromethylated 2-oxindoles
    Chan, Chun-Wo
    Lee, Pui-Yiu
    Yu, Wing-Yiu
    TETRAHEDRON LETTERS, 2015, 56 (20) : 2559 - 2563
  • [34] Metal-Free Aerobic Oxidative C-O Coupling of C(sp3)-H with Carboxylic Acids Catalyzed by DDQ and tert-Butyl Nitrite
    Pan, Decheng
    Pan, Zilong
    Hu, Zhiming
    Li, Meichao
    Hu, Xinquan
    Jin, Liqun
    Sun, Nan
    Hu, Baoxiang
    Shen, Zhenlu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (33) : 5650 - 5655
  • [35] Palladium(II)-Catalyzed Dehydrogenative Cross-Coupling between Two Csp3-H Bonds: Unexpected C=C Bond Formation
    Li, Gaocan
    Qian, Shengyou
    Wang, Chunxia
    You, Jingsong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (30) : 7837 - 7840
  • [36] Palladium(II)-Catalyzed Intramolecular Oxidative C-H/C-H Cross-Coupling Reaction of C3,N-Linked Biheterocycles: Rapid Access to Polycyclic Nitrogen Heterocycles
    Mantenuto, Serena
    Ciccolini, Cecilia
    Lucarini, Simone
    Piersanti, Giovanni
    Favi, Gianfranco
    Mantellini, Fabio
    ORGANIC LETTERS, 2017, 19 (03) : 608 - 611
  • [37] Palladium-catalyzed oxidative C-H/C-H cross-coupling of 1-substituted 1,2,3-triazoles with furans and thiophenes
    Yu, Xin
    Huang, ZhenDong
    Liu, Wei
    Shi, SuPing
    Kuang, ChunXiang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (15) : 4459 - 4465
  • [38] Palladium-catalyzed cross-coupling of 2-iodobiphenyls with ortho-chloroacetophenones through dual C-H arylation for the construction of tribenzo[a,c,f]cyclooctanones
    Zuo, Xiang
    Cheng, Cang
    Zhang, Yanghui
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (18): : 4937 - 4942
  • [39] The First Example of Palladium(II)-Catalyzed Oxidative C–N Cross Coupling of 2H-Imidazole 1-Oxide with Azoles
    Alexey A. Akulov
    Mikhail V. Varaksin
    Valery N. Charushin
    Oleg N. Chupakhin
    Chemistry of Heterocyclic Compounds, 2019, 55 : 783 - 787
  • [40] Oxidative cross-dehydrogenative coupling (CDC) -H bond functionalization:butyl peroxybenzoate (TBPB)-promoted regioselective direct C-3 acylation/benzoylation of 2-indazoles with aldehydes/benzyl alcohols/styrenes
    Sharma, Richa
    Yadav, Lalit
    Yadav, Ravi Kant
    Chaudhary, Sandeep
    RSC ADVANCES, 2021, 11 (23) : 14178 - 14192
12345