Palladium-catalyzed one-pot Catellani reaction: An efficient synthesis of α-alkynyl aromatic ketones via ortho acylation and ipso alkynylation

被引：7
作者：
Yu, Shao-Peng [1 ]
Zhong, Yue [1 ]
Gu, Ting [1 ]
Wu, Wen-Yu [1 ]
Fan, Tian Yuan [1 ]
Li, Nian-Guang [1 ]
Shi, Zhi-Hao [2 ]
Tang, Yu-Ping [1 ,3 ,4 ]
Duan, Jin-Ao [1 ]
机构：
[1] Nanjing Univ Chinese Med, Jiangsu Key Lab High Technol Res TCM Formulae, Jiangsu Collaborat Innovat Ctr Chinese Med Resour, Natl & Local Collaborat Engn Ctr Chinese Med Reso, Nanjing 210023, Jiangsu, Peoples R China
[2] China Pharmaceut Univ, Dept Organ Chem, Nanjing 211198, Jiangsu, Peoples R China
[3] Shaanxi Univ Chinese Med, Coll Pharm, Xian 712046, Shaanxi, Peoples R China
[4] Shaanxi Univ Chinese Med, Shaanxi Collaborat Innovat Ctr Chinese Med Resour, Xian 712046, Shaanxi, Peoples R China
来源：
TETRAHEDRON | 2018年 / 74卷 / 40期
关键词：
Catellani reaction; Acylation; Alkynylation; 2-Alkynyl aromatic ketones; Palladium-catalyzed; C-H FUNCTIONALIZATION; ARYL IODIDES; REGIOSPECIFIC SYNTHESIS; ALKYLATION; PD/NORBORNENE; ACTIVATION; ANNULATION; AMINATION;
D O I：
10.1016/j.tet.2018.08.027
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A palladium-catalyzed and norbornene-mediated Catellani reaction was developed through ortho-acylation and ipso-alkynylation for the aryl iodides. Acyl chlorides were used as acylation reagents and phenylpropiolic acids were used as termination reagents respectively in this transformation. As a result, the reactivity of these three different compounds matched well and this unreported combination could be used extensively. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5942 / 5949
页数：8
相关论文
共 50 条
  • [21] Synthesis of β-alkynyl α-amino acids via palladium-catalyzed alkynylation of unactivated C(sp3)-H bonds
    Bo Wang
    Gang He
    Gong Chen
    Science China Chemistry, 2015, 58 : 1345 - 1348
  • [22] An Approach to One-Pot Regioselective Synthesis of Indenones through Palladium-Catalyzed Annulation in Water
    Ramesh, Karu
    Satyanarayana, Gedu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (30) : 4135 - 4146
  • [23] One-Pot Synthesis of Diarylmethylidenefluorenes and Phenanthrenes by Palladium-Catalyzed Multiple C-H Bond Functionalization
    Thirunavukkarasu, Vedhagiri S.
    Parthasarathy, Kanniyappan
    Cheng, Chien-Hong
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (05) : 1436 - 1440
  • [24] Palladium-Catalyzed Divergent Arylation with Triazolopyridines: One-Pot Synthesis of 6-Aryl-2-α-styrylpyridines
    Moon, Youngtaek
    Kwon, Soonhyung
    Kang, Dahye
    Im, Honggu
    Hong, Sungwoo
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (06) : 958 - 964
  • [25] One-Pot Palladium(II)-Catalyzed Synthesis of Fluorenones via Decarboxylative Cyclization
    Cai, Zhiqiang
    Hou, Xu
    Hou, Ling
    Hu, Zhiquan
    Zhang, Bo
    Jin, Zhengsheng
    SYNLETT, 2016, 27 (03) : 395 - 398
  • [26] Palladium-Catalyzed One-Pot Carbonylative Sonogashira Reaction Employing Formic acid as the CO Source
    Qi, Xinxin
    Jiang, Li-Bing
    Li, Chong-Liang
    Li, Rui
    Wu, Xiao-Feng
    CHEMISTRY-AN ASIAN JOURNAL, 2015, 10 (09) : 1870 - 1873
  • [27] One-Pot Palladium-Catalyzed Cross-Coupling Treble of Borylation, the Suzuki Reaction and Amination
    Jong, Howard
    Eey, Stanley T. -C.
    Lim, Yee Hwee
    Pandey, Sangeeta
    Iqbal, Nurul Azmah Bte
    Yong, Fui Fong
    Robins, Edward G.
    Johannes, Charles W.
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (04) : 616 - 622
  • [28] Photocatalytic One-Pot Synthesis of Homoallyl Ketones via a Norrish Type I Reaction of Cyclopentanones
    Okada, Megumi
    Yamada, Keiichi
    Fukuyama, Takahide
    Ravelli, Davide
    Fagnoni, Maurizio
    Ryu, Ilhyong
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (18) : 9365 - 9369
  • [29] Palladium-Catalyzed One-Pot Synthesis of via 1H-indole-3-sulfonates Generated in Situ from 2-Alkynyl Arylazides and Sulfonic Acids
    Zhang, Xiaoxiang
    Li, Ping
    Lyu, Chang
    Yong, Wanxiong
    Li, Jing
    Pan, Xinyu
    Zhu, Xinbao
    Rao, Weidong
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (23) : 4147 - 4152
  • [30] Facile One-Pot Palladium-Catalyzed Sequential Coupling to Diarylmethanes by Using Aryl Methyl Ketones as the Methylene Donors
    Wang, Xing
    Liu, Lian-Hua
    Shi, Jin-Hua
    Peng, Ji
    Tu, Hai-Yang
    Zhang, Ai-Dong
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (30) : 6870 - 6877
12345