Rhodium-Catalyzed Annulation of 4-Arylbut-3-yn-1-amines with Internal Alkynes through C-H Functionalization

被引：23
作者：
Li, Yang [1 ]
Pi, Rui [1 ]
Ouyang, Xuan-Hui [1 ]
Song, Ren-Jie [1 ]
Li, Jin-Heng [1 ,2 ]
机构：
[1] Nanchang Hangkong Univ, Key Lab Jiangxi Prov Persistent Pollutants Contro, Nanchang 330063, Jiangxi, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 02期
基金：
中国国家自然科学基金;
关键词：
INTRAMOLECULAR CYCLIZATION; C(SP(3))-H ACTIVATION; BOND FORMATION; CYCLOADDITION; CONSTRUCTION; ALKYNYLATION; TRANSFORMATIONS; ACRYLAMIDES; ANTIFUNGAL; AMIDATION;
D O I：
10.1021/acs.orglett.8b03561
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new, one-step rhodium(III)-catalyzed annulation of 4-arylbut-3-yn-1-amines with internal alkynes through C-H functionalization is reported. This reaction allows the formation of three new chemical bonds, including two C-C bonds and one C-N band, thus selectively assembling various spiro[indene-1,2'-pyrrolidine]s with excellent functional group compatibility, high atom-economy, and step-efficiency.
引用
收藏
页码：397 / 400
页数：4
相关论文
共 79 条
  • [21] NITRILE OXIDES IN MEDICINAL CHEMISTRY .2. SYNTHESIS OF THE 2 ENANTIOMERS OF DIHYDROMUSCIMOL
    DEAMICI, M
    DEMICHELI, C
    MISANI, V
    [J]. TETRAHEDRON, 1990, 46 (06) : 1975 - 1986
  • [22] Experimental and computational studies on H2O-promoted, Rh-catalyzed transient-ligand-free ortho-C(sp2)-H amidation of benzaldehydes with dioxazolones
    Ding, Jun
    Jiang, Wei
    Bai, He-Yuan
    Ding, Tong-Mei
    Gao, Dafang
    Bao, Xiaoguang
    Zhang, Shu-Yu
    [J]. CHEMICAL COMMUNICATIONS, 2018, 54 (64) : 8889 - 8892
  • [23] Rhodium(III)-catalyzed olefinic C-H alkynylation of enamides at room temperature
    Feng, Chao
    Feng, Daming
    Loh, Teck-Peng
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (69) : 9865 - 9868
  • [24] Rh(III)-Catalyzed C-H Activation with Allenes To Synthesize Conjugated Olefins
    Gong, Tian-Jun
    Su, Wei
    Liu, Zhao-Jing
    Cheng, Wan-Min
    Xiao, Bin
    Fu, Yao
    [J]. ORGANIC LETTERS, 2014, 16 (02) : 330 - 333
  • [25] Rh[III]-Catalyzed C-H Amidation Using Aroyloxycarbamates To Give N-Boc Protected Arylamines
    Grohmann, Christoph
    Wang, Honggen
    Glorius, Frank
    [J]. ORGANIC LETTERS, 2013, 15 (12) : 3014 - 3017
  • [26] Metal-Catalyzed Annulations through Activation and Cleavage of C-H Bonds
    Gulias, Moises
    Luis Mascarenas, Jose
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (37) : 11000 - 11019
  • [27] Copper-Catalyzed C-H Functionalization Reactions: Efficient Synthesis of Heterocycles
    Guo, Xun-Xiang
    Gu, Da-Wei
    Wu, Zhengxing
    Zhang, Wanbin
    [J]. CHEMICAL REVIEWS, 2015, 115 (03) : 1622 - 1651
  • [28] Synthesis of [5,6]-Bicyclic Heterocycles with a Ring-Junction Nitrogen Atom: Rhodium(III)-Catalyzed C-H Functionalization of Alkenyl Azoles
    Halskov, Kim Soholm
    Roth, Howard S.
    Ellman, Jonathan A.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (31) : 9183 - 9187
  • [29] Rhodium-catalyzed selective C-H functionalization of NNN tridentate chelating compounds via a rollover pathway
    Hong, Seung Youn
    Kwak, Jaesung
    Chang, Sukbok
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (15) : 3159 - 3162
  • [30] Rh(III)-Catalyzed Addition of Alkenyl C-H Bond to Isocyanates and Intramolecular Cyclization: Direct Synthesis 5-Ylidenepyrrol-2(5H)-ones
    Hou, Wei
    Zhou, Bing
    Yang, Yaxi
    Feng, Huijin
    Li, Yuanchao
    [J]. ORGANIC LETTERS, 2013, 15 (08) : 1814 - 1817
12345678