Palladium-Catalyzed Tandem Fluorination and Cyclization of Enynes

被引：86
|
作者：
Peng, Haihui [1 ]
Liu, Guosheng [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 04期
关键词：
ARYL FLUORIDES; BOND FORMATION; STEREOSELECTIVE-SYNTHESIS; METAL CATALYSIS; ALKYNES; REACTIVITY; CONVERSION; MOLECULES; STATE;
D O I：
10.1021/ol103039x
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel palladium-catalyzed tandem fluorination and cyclization of enynes has been developed. A favorable cis-fluoropalladation is proposed as a key step to construct a vinyl-F bond, and the final C-5p3-Pd bond is reduced by alcohol. This transformation represents an efficient road to synthesize fluorinated lactams.
引用
收藏
页码：772 / 775
页数：4
相关论文
共 50 条
  • [31] Palladium-catalyzed cyclization of enediynes to benzopyranones
    Chang, Wei-Ren
    Lo, Yu-Hsiang
    Lee, Chia-Ying
    Wu, Ming-Jung
    ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (09) : 1248 - 1252
  • [32] Palladium-Catalyzed Cyclization of Alkenes with Organohalides
    Chu, Xue-Qiang
    Liu, Dan
    Xing, Zhen-Hua
    Xu, Xiao-Ping
    Ji, Shun Jun
    ORGANIC LETTERS, 2016, 18 (04) : 776 - 779
  • [33] Palladium-Catalyzed Carbonylative Cyclization of Azoarenes
    Wang, Zechao
    Yin, Zhiping
    Zhu, Fengxiang
    Li, Yahui
    Wu, Xiao-Feng
    CHEMCATCHEM, 2017, 9 (19) : 3637 - 3640
  • [34] SPANphos Ligands in Palladium-Catalyzed Asymmetric Fluorination
    Jacquet, Olivier
    Clement, Nicolas D.
    Blanco, Carolina
    Martinez Belmonte, Marta
    Benet-Buchholz, Jordi
    van Leeuwen, Piet W. N. M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (25) : 4844 - 4852
  • [35] Mechanistic Investigations of Palladium-Catalyzed Allylic Fluorination
    Katcher, Matthew H.
    Norrby, Per-Ola
    Doyle, Abigail G.
    ORGANOMETALLICS, 2014, 33 (09) : 2121 - 2133
  • [36] PALLADIUM-CATALYZED SYNTHESIS OF SILYL-SUBSTITUTED ENYNES
    ISHIKAWA, M
    OHSHITA, J
    ITO, Y
    MINATO, A
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 346 (03) : C58 - C60
  • [37] Further studies on palladium-catalyzed bismetallative cyclization of enynes in the presence of Bu3SnSiMe3
    Sato, Y
    Imakuni, N
    Hirose, T
    Wakamatsu, H
    Mori, M
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 687 (02) : 392 - 402
  • [38] PALLADIUM-CATALYZED ALKYLATIVE CYCLIZATION OF IODONIUM SALTS WITH ENYNES - A MILD AND STEREOSELECTIVE REACTION USING HYPERVALENT IODINE
    MORIARTY, RM
    BOOTH, DT
    BRUMER, H
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 210 : 397 - ORGN
  • [39] Palladium-Catalyzed Carbo-Aminative Cyclization of 1,6-Enynes: Access to Napthyridinone Derivatives
    Babu, Undamatla Suri
    Singam, Maneesh Kumar Reddy
    Kumar, Muniganti Naveen
    Nanubolu, Jagadeesh Babu
    Reddy, Maddi Sridhar
    ORGANIC LETTERS, 2022, 24 (08) : 1598 - 1603
  • [40] Palladium-catalyzed tandem addition/cyclization in aqueous medium: synthesis of 2-arylindoles
    Yu, Shuling
    Hu, Kun
    Gong, Julin
    Qi, Linjun
    Zhu, Jianghe
    Zhang, Yetong
    Cheng, Tianxing
    Chen, Jiuxi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (20) : 4300 - 4307
12345