Palladium-Catalyzed Direct C-H Arylation of Cyclic Enaminones with Aryl Iodides

被引:36
|
作者
Yu, Yi-Yun
Bi, Lei
Georg, Gunda I. [1 ]
机构
[1] Univ Minnesota, Dept Chem, Dept Med Chem, Minneapolis, MN 55414 USA
来源
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 12期
基金
美国国家卫生研究院;
关键词
PALLADIUM(II)-CATALYZED DIRECT ARYLATION; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; COUPLING REACTIONS; ALKALOIDS; MECHANISM; METATHESIS; COMPLEXES; HALIDES;
D O I
10.1021/jo400830t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A ligand-free method for the Pd-catalyzed direct arylation of cyclic enaminones using aryl iodides was developed. This method can be applied to a wide range of cyclic enaminones and aryl iodides with excellent C5-regioselectivity. Using widely available aryl iodides, the generality of this transformation provides easy access to a variety of 3-arylpiperidine structural motifs.
引用
收藏
页码:6163 / 6169
页数:7
相关论文
共 50 条
  • [31] Palladium-Catalyzed Trifluoromethylthiolation of Aryl C-H Bonds
    Xu, Chunfa
    Shen, Qilong
    ORGANIC LETTERS, 2014, 16 (07) : 2046 - 2049
  • [32] Palladium-Catalyzed Decarboxylative C-H Bond Arylation of Thiophenes
    Hu, Peng
    Zhang, Min
    Jie, Xiaoming
    Su, Weiping
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (01) : 227 - 231
  • [33] Palladium-Catalyzed Direct C-H Arylation of Arenes Promoted by Quaternary Ammonium Salt
    Yang, Sabyuk
    Hong, Soon Hyeok
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (11) : 1846 - 1851
  • [34] Palladium-Catalyzed Direct C-H Arylation of 3-Butenoic Acid Derivatives
    Yang, Shan
    Liu, Lingling
    Zhou, Zheng
    Huang, Zhibin
    Zhao, Yingsheng
    ORGANIC LETTERS, 2021, 23 (02) : 296 - 299
  • [35] Enhancing the regioselectivity of C-H activation in palladium-catalyzed direct arylation polymerization (DARP)
    Woods, Keenan
    Wiley, Calvin
    Simmons, Bryan
    Boggess, Steven
    Rudenko, Andrey
    Thompson, Barry C.
    Tannaci, John F.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [36] Palladium-Catalyzed Decarboxylative C-H Bond Arylation of Furans
    Pei, Kai
    Jie, Xiaoming
    Zhao, Huaiqing
    Su, Weiping
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (20) : 4230 - 4233
  • [37] Palladium-Catalyzed Domino Heck/C-H Activation/Intermolecular Direct Arylation Reactions
    Lu, Zhiyao
    Cui, Yuxin
    Jia, Yanxing
    SYNTHESIS-STUTTGART, 2011, (16): : 2595 - 2599
  • [38] Palladium-Catalyzed Direct Arylation of Azulene Based on Regioselective C-H Bond Activation
    Murai, Masahito
    Yanagawa, Mayu
    Nakamura, Masahiro
    Takai, Kazuhiko
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (05) : 629 - 635
  • [39] Palladium-Catalyzed C-H Arylation of Amides by Triazole Assistance
    Santrac, Darko
    Cella, Stefano
    Wang, Wei
    Ackermann, Lutz
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (32) : 5429 - 5436
  • [40] Palladium-Catalyzed β-C-H Arylation of Alkyl Carboxamides with Sterically Hindered Aryl Iodides Using ortho-Sulfinyl Aniline Auxiliaries
    Mu, Delong
    Gao, Fang
    Chen, Gong
    He, Gang
    ACS CATALYSIS, 2017, 7 (03): : 1880 - 1885