Palladium-Catalyzed Denitrative α-Arylation of Heteroarenes with Nitroarenes via C-H and C-NO2 Bond Activations

被引:6
作者
Yao, Jiaxin [1 ]
Xiao, Yuxuan [1 ]
Li, Haiyan [1 ]
Yang, Xun [1 ]
Du, Jiahui [1 ]
Yin, Ying [1 ]
Feng, Lin [1 ]
Duan, Wengui [1 ]
Yu, Lin [1 ]
机构
[1] Guangxi Univ, Key Lab Appl Chem Technol & Resource Dev, Guangxi Coll & Univ, Sch Chem & Chem Engn, Nanning 530004, Guangxi, Peoples R China
关键词
ARYL; FUNCTIONALIZATION; (HETERO)ARENES; LIGAND; MILD;
D O I
10.1021/acs.orglett.4c02340
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general approach for the alpha-arylation of heteroarenes with nitroarenes via denitrative coupling is reported for the first time. Various heteroarenes, including derivatives of furan, benzofuran, pyrrole, indole, thiophene, and benzothiophene, can be arylated at the alpha-position in moderate to good yields. Mechanistic studies demonstrate that the reaction proceeds via a CMD pathway, with C-H bond activation as the rate-determining step. Furthermore, the scalability and applicability in the synthesis of a drug molecule exemplify the utility of this protocol.
引用
收藏
页码:7307 / 7312
页数:6
相关论文
共 48 条
  • [1] Sustainable protocols for direct C-H bond arylation of (hetero)arenes
    Albano, Gianluigi
    Punzi, Angela
    Capozzi, Maria Annunziata M.
    Farinola, Gianluca M.
    [J]. GREEN CHEMISTRY, 2022, 24 (05) : 1809 - 1894
  • [2] Pd-Catalyzed Denitrative Intramolecular C-H Arylation
    Asahara, Kitty K.
    Okita, Toshimasa
    Saito, Ami N.
    Muto, Kei
    Nakao, Yoshiaki
    Yamaguchi, Junichiro
    [J]. ORGANIC LETTERS, 2019, 21 (12) : 4721 - 4724
  • [3] Facile access to nitroarenes and nitroheteroarenes using N-nitrosaccharin
    Calvo, Roxan
    Zhang, Kun
    Passera, Alessandro
    Katayev, Dmitry
    [J]. NATURE COMMUNICATIONS, 2019, 10 (1)
  • [4] Construction of Heterobiaryl Skeletons through Pd-Catalyzed Cross-Coupling of Nitroarenes and Heterocyclic Arylborononate Esters with a Sterically Demanding NHC Ligand
    Chen, Wei
    Chen, Wanzhi
    Liu, Miaochang
    Wu, Huayue
    [J]. ORGANIC LETTERS, 2022, : 6983 - 6987
  • [5] Ag(I)-C-H Activation Enables Near-Room-Temperature Direct α-Arylation of Benzo[b]thiophenes
    Colletto, Chiara
    Panigrahi, Adyasha
    Fernandez-Casado, Jaime
    Larrosa, Igor
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (30) : 9638 - 9643
  • [6] A palladium- catalyzed regiocontrollable hydroarylation reaction of allenamides with B2pin2/ H2O+
    Cui, Jie
    Meng, Long
    Chi, Xiaochen
    Liu, Qing
    Zhao, Pingping
    Zhang, Dao-peng
    Chen, Lei
    Li, Xinjin
    Dong, Yunhui
    Liu, Hui
    [J]. CHEMICAL COMMUNICATIONS, 2019, 55 (30) : 4355 - 4358
  • [7] From Nature to Drug Discovery: The Indole Scaffold as a 'Privileged Structure'
    de Sa Alves, Fernando Rodrigues
    Barreiro, Eliezer J.
    Manssour Fraga, Carlos Alberto
    [J]. MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2009, 9 (07) : 782 - 793
  • [8] A methylation platform of unconventional inert aryl electrophiles: trimethylboroxine as a universal methylating reagent
    Feng, Boya
    Yang, Yudong
    You, Jingsong
    [J]. CHEMICAL SCIENCE, 2020, 11 (23) : 6031 - 6035
  • [9] Palladium-catalyzed denitrative Sonogashira-type cross-coupling of nitrobenzenes with terminal alkynes
    Feng, Boya
    Yang, Yudong
    You, Jingsong
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (05) : 790 - 793
  • [10] Palladium-catalyzed denitrative N-arylation of nitroarenes with pyrroles, indoles, and carbazoles
    Feng, Lin
    Yao, Jiaxin
    Yu, Lin
    Duan, Wengui
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (09) : 2351 - 2356