Palladium-Catalyzed Hydroaminocarbonylation of Alkynes with Tertiary Amines via C-N Bond Cleavage

被引:66
|
作者
Gao, Bao [1 ]
Huang, Hanmin [1 ,2 ,3 ]
机构
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China
[3] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
基金
中国国家自然科学基金;
关键词
CARBON-NITROGEN BOND; ALPHA; BETA-UNSATURATED AMIDES; DEALKYLATIVE CARBONYLATION; REGIOSELECTIVE SYNTHESIS; MONO(AMINE) COMPLEXES; ANILINE DERIVATIVES; SAMARIUM DIIODIDE; ARYL IODIDES; ACTIVATION; AMINALS;
D O I
10.1021/acs.orglett.7b03331
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient strategy for the cleavage of the CN bond of tertiary amines was developed with DTBP as an oxidant, in which the cleaved H atom and amine moiety were successfully transferred to the desired products. This strategy has enabled an efficient palladium-catalyzed hydroaminocarbonylation of alkynes with tertiary amines. Notably, the catalyst loading could be lowered from 5 to 0.1 mol %, which represents the lowest catalyst loading among the reported work on carbonylation via CN bond activation.
引用
收藏
页码:6260 / 6263
页数:4
相关论文
共 50 条
  • [21] Palladium-Catalyzed Aminomethylamination and Aromatization of Aminoalkenes with Aminals via C-N Bond Activation
    Li, Lixin
    Liu, Peipei
    Su, Yijin
    Huang, Hanmin
    [J]. ORGANIC LETTERS, 2016, 18 (21) : 5736 - 5739
  • [22] Palladium-Catalyzed Oxidative N-Dealkylation/Carbonylation of Tertiary Amines with Alkynes to α,β-Alkynylamides
    Mane, Rajendra S.
    Bhanage, Bhalchandra M.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (12): : 4974 - 4980
  • [23] An efficient and straightforward approach for accessing thionoesters via palladium-catalyzed C-N cleavage of thioamides
    Liu, Yinbo
    Mo, Xiaofeng
    Majeed, Irfan
    Zhang, Mei
    Wang, Hui
    Zeng, Zhuo
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (07) : 1532 - 1537
  • [24] Palladium-Catalyzed C-P Cross-Coupling of Arylhydrazines with H-Phosphonates via C-N Bond Cleavage
    Xu, Wentao
    Hu, Gaobo
    Xu, Pengxiang
    Gao, Yuxing
    Yin, Yingwu
    Zhao, Yufen
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (14-15) : 2948 - 2954
  • [25] Palladium-catalyzed carbonylation of allylamines via C-N bond activation leading to β,γ-unsaturated amides
    Yu, Hui
    Zhang, Guoying
    Liu, Zong-Jian
    Huang, Hanmin
    [J]. RSC ADVANCES, 2014, 4 (109): : 64235 - 64237
  • [26] Palladium-Catalyzed Hydroaminocarbonylation of Olefins with Aliphatic Amines without Additives
    Bede, Fanni
    Kollar, Laszlo
    Lambert, Nandor
    Huszthy, Peter
    Pongracz, Peter
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (31)
  • [27] Iodine-catalyzed C3-formylation of indoles via C-N bond cleavage of tertiary amines under aerobic conditions
    Lu, Lin
    Xiong, Qiheng
    Guo, Shengmei
    He, Tianqiang
    Xu, Feng
    Gong, Jiuhan
    Zhu, Zheng
    Cai, Hu
    [J]. TETRAHEDRON, 2015, 71 (22) : 3637 - 3641
  • [28] Palladium-Catalyzed Decarbonylation of Amino Acid Derivatives via C-C Bond and C-N Bond Dual Activations
    Wu, Jiamin
    Zhang, Jinli
    Jiao, Yongjuan
    Deng, Gongtao
    Li, Yingmei
    Zhang, Zhengyu
    Jiang, Yaojia
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23): : 17462 - 17470
  • [29] Palladium-catalyzed hydroaminocarbonylation of alkenes with amines promoted by weak acid
    Zhang, Guoying
    Ji, Xiaolei
    Yu, Hui
    Yang, Lei
    Jiao, Peng
    Huang, Hanmin
    [J]. TETRAHEDRON LETTERS, 2016, 57 (03) : 383 - 386
  • [30] Transalkylation via C-N Bond Cleavage of Amines Catalyzed by Super Organophotoreductant CBZ6
    Chen, Yong-Ze
    Chen, Yi-Ming
    Hu, Yuan
    Qu, Jian-Ping
    Kang, Yan-Biao
    [J]. ORGANIC LETTERS, 2023, : 7518 - 7522