Palladium-catalyzed intramolecular Cp-H bond functionalization/arylation: an enantioselective approach to planar chiral quinilinoferrocenes

被引：63
|
作者：
Ma, Xinna [1 ]
Gu, Zhenhua [1 ]
机构：
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
来源：
RSC ADVANCES | 2014年 / 4卷 / 68期
关键词：
TRANSITION-METAL-COMPLEXES; ASYMMETRIC CATALYSIS; FERROCENE DERIVATIVES; ARENE CHROMIUM; HECK REACTION; LIGANDS; METALLOCENES; METHOXYCARBONYLATION; DESYMMETRIZATION; HETEROCYCLES;
D O I：
10.1039/c4ra07832b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A palladium-catalyzed intramolecular asymmetric Cp-H functionalization/cyclization reaction to construct planar chiral quinilinoferrocenes was reported. The current investigation indicated that Carriera's O-PINAP ligands gave the best enantiomeric induction. The palladium-catalyzed reaction allowed a variety of chiral quinilinoferrocenes to be synthesized with broad functional group tolerance.
引用
收藏
页码：36241 / 36244
页数：4
相关论文
共 50 条
  • [21] Highly regioselective C-H bond functionalization: palladium-catalyzed arylation of substituted imidazo[1,2-a]pyridine with aryl chlorides
    Cao, Hua
    Lin, Yuanguang
    Zhan, Haiying
    Du, Zuodong
    Lin, Xiulian
    Liang, Qi-Mei
    Zhang, Hong
    RSC ADVANCES, 2012, 2 (14) : 5972 - 5975
  • [22] Axially Chiral Dibenzazepinones by a Palladium(0)-Catalyzed Atropo-enantioselective C-H Arylation
    Newton, Christopher G.
    Braconi, Elena
    Kuziola, Jennifer
    Wodrich, Matthew D.
    Cramer, Nicolai
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (34) : 11040 - 11044
  • [23] Palladium-catalyzed tandem cyclization of bromoenynes through aromatic C-H bond functionalization
    Ohno, H
    Yamamoto, M
    Iuchi, M
    Tanaka, T
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (32) : 5103 - 5106
  • [24] Access to chiral tetrahydrofluorenes through a palladium-catalyzed enantioselective tandem intramolecular Heck/Tsuji-Trost reaction
    Zhang, Ying
    Shen, Hong-Cheng
    Li, Yang-Yang
    Huang, Yong-Shuang
    Han, Zhi-Yong
    Wu, Xiang
    CHEMICAL COMMUNICATIONS, 2019, 55 (26) : 3769 - 3772
  • [25] Mechanistic Model for Enantioselective Intramolecular Alkene Cyanoamidation via Palladium-Catalyzed C-CN Bond Activation
    Frost, Grant B.
    Serratore, Nicholas A.
    Ogilvie, Jodi M.
    Douglas, Christopher J.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (07) : 3721 - 3726
  • [26] Palladium-Catalyzed Direct and Regioselective C-H Bond Functionalization/Oxidative Acetoxylation of Indoles
    Choy, Pui Ying
    Lau, Chak Po
    Kwong, Fuk Yee
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (01) : 80 - 84
  • [27] Enantioselective Synthesis of N-N Atropisomers by Palladium-Catalyzed C-H Functionalization of Pyrroles
    Yao, Wang
    Lu, Chuan-Jun
    Zhan, Li-Wen
    Wu, Yi
    Feng, Jia
    Liu, Ren-Rong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (21)
  • [28] Palladium-Catalyzed Highly Enantioselective Arylation of Cyclic N-Sulfonyl α-Ketimino Esters towards the Synthesis of α-Quaternary Chiral Amino Acid Derivatives
    Wu, Chun-Yan
    Xu, Ming-Hua
    CHEMCATCHEM, 2020, 12 (04) : 1129 - 1133
  • [29] Palladium-Catalyzed Intramolecular Aryl Amination Reaction: An Expeditious Approach to the Synthesis of Chiral Benzodiazocine Derivatives
    Das Adhikary, Nirmal
    Chattopadhyay, Partha
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (09) : 1754 - 1762
  • [30] Chiral Bifunctional Phosphine-Carboxylate Ligands for Palladium(0)-Catalyzed Enantioselective C-H Arylation
    Yang, Lei
    Neuburger, Markus
    Baudoin, Olivier
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (05) : 1394 - 1398
12345