Facile Construction of Functionalized 4H-Chromene Scaffolds via Sn(OTf)2-Catalyzed C-H Functionalization/Cyclization Reaction and Ir-Catalyzed Direct C-H Amidation

被引:0
|
作者
Qi, Hongbo [1 ]
He, Junxia [1 ]
Yuan, Xingyu [1 ]
Chen, Shufeng [1 ]
机构
[1] Inner Mongolia Univ, Dept Chem & Chem Engn, Inner Mongolia Key Lab Fine Organ Synth, Hohhot 010021, Peoples R China
基金
中国国家自然科学基金;
关键词
amination; 4H-chromenes; cyclization; C-H functionalization; Lewis acid; N BOND FORMATION; SELECTIVE SYNTHESIS; TANDEM REACTION; EFFICIENT; ACCESS; LIGAND; IDENTIFICATION; DISCOVERY; PRINCIPLE; AMINATION;
D O I
10.1002/ajoc.202300140
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient strategy for the construction of 4H-chromene scaffolds from naphthols and conjugated diketones through a sequential Sn(OTf)(2)-catalyzed Friedel-Crafts type C-H functionalization/cyclization process has been described. The Ir-catalyzed C-H amination of these products could also be performed with the assistance of the carbonyl as a weak directing group, which produced a series of amino-modified 4H-chromene compounds in good yields.
引用
收藏
页数:5
相关论文
共 50 条
  • [1] Ir-Catalyzed Functionalization of C-H Bonds
    Choi, Jongwook
    Goldman, Alan S.
    IRIDIUM CATALYSIS, 2011, 34 : 139 - 167
  • [2] Ir-Catalyzed C-H Amidation and Borylation of Anthraquinones
    Camelio, Andrew M.
    Wright, Robert J.
    Knight, Nicole T.
    Jazdzewski, Brian A.
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (08): : 4940 - 4947
  • [3] Ir-catalyzed C-H silylations of phenyldeazapurines
    Sabat, Nazarii
    Slavetinska, Lenka Postova
    Hocek, Michal
    TETRAHEDRON LETTERS, 2015, 56 (49) : 6860 - 6862
  • [4] Synthesis of Phosphoramidates: A Facile Approach Based on the C-N Bond Formation via Ir-Catalyzed Direct C-H Amidation
    Kim, Hyunwoo
    Park, Juhyeon
    Kim, Jeung Gon
    Chang, Sukbok
    ORGANIC LETTERS, 2014, 16 (20) : 5466 - 5469
  • [5] Electrochemistry-Enabled Ir-Catalyzed Vinylic C-H Functionalization
    Yang, Qi-Liang
    Xing, Yi-Kang
    Wang, Xiang-Yang
    Ma, Hong-Xing
    Weng, Xin-Jun
    Yang, Xiang
    Guo, Hai-Ming
    Mei, Tian-Sheng
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (48) : 18970 - 18976
  • [6] Ir-Catalyzed C-H Amidation of Aldehydes with Stoichiometric/Catalytic Directing Group
    Zhang, Yun-Fei
    Wu, Bin
    Shi, Zhang-Jie
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (49) : 17808 - 17812
  • [7] Synthesis of Lactams via Ir-Catalyzed C-H Amidation Involving Ir-Nitrene Intermediates
    Liu, Jitian
    Ye, Wenjing
    Wang, Shuojin
    Zheng, Junrong
    Tang, Weiping
    Li, Xiaoxun
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (06): : 4430 - 4440
  • [8] Ir-Catalyzed C-H Amidation Using Carbamoyl Azides for the Syntheses of Unsymmetrical Ureas
    Yoo, Kwangho
    Lee, Jooyeon
    Park, Myung Hwan
    Kim, Youngjo
    Kim, Hyun Jin
    Kim, Min
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (09): : 6233 - 6241
  • [9] Palladium-catalyzed enantioselective C-H functionalization via C-H palladation
    Zhan, Bei-Bei
    Jin, Liang
    Shi, Bing-Feng
    TRENDS IN CHEMISTRY, 2022, 4 (03): : 220 - 235
  • [10] Facile construction of functionalized 4H-chromene via tandem benzylation and cyclization
    Fan, Jinmin
    Wang, Zhiyong
    CHEMICAL COMMUNICATIONS, 2008, (42) : 5381 - 5383