Metal-Free Catalytic Approach for Allylic C-H Amination Using N-Heterocycles via sp3 C-H Bond Activation

被引:36
|
作者
Sun, Jinwei [1 ]
Wang, Yi [1 ]
Pan, Yi [1 ]
机构
[1] Nanjing Univ, Sch Chem & Chem Engn, Nanjing 210093, Jiangsu, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 18期
基金
中国国家自然科学基金;
关键词
EFFICIENT SYNTHESIS; DEHYDROGENATIVE FUNCTIONALIZATION; ORGANOCATALYTIC AMINATION; ALLYLAMINE DERIVATIVES; COUPLING REACTIONS; TERMINAL ALKENES; SIMPLE OLEFINS; ALKYLATION; OXIDATION; STRATEGY;
D O I
10.1021/acs.joc.5b01383
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A versatile metal-free synthesis of allylic N-heterocycles has been developed using a TBAI/TBHP oxidation system. This general protocol could be applied for the C-N bond formation of electron-deficient phthalimides, imidazoles, triazoles, and sulfonamides with cyclic and acylic olefins. The practical use of the method is demonstrated by the amidation of functionalized biologically active substrates.
引用
收藏
页码:8945 / 8950
页数:6
相关论文
共 50 条
  • [1] Arylation of Saturated N-Heterocycles via sp3 C-H Activation
    Schnuerch, M.
    Sames, D.
    [J]. JOINT MEETING ON MEDICAL CHEMISTRY, 2009, : 27 - +
  • [2] Catalytic Metal-free Allylic C-H Amination of Terpenoids
    Teh, Wei Pin
    Obenschain, Derek C.
    Black, Blaise M.
    Michael, Forrest E.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (39) : 16716 - 16722
  • [3] Metal-Free Allylic C-H Amination
    Murakami S.
    [J]. Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 2023, 81 (03): : 267 - 268
  • [4] Metal-Free Allylic C-H Amination
    Murakami, Suguru
    [J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2023, 81 (03) : 267 - 268
  • [5] Metal-free oxidative C-C bond formation of active methylenic sp3 C-H bonds with benzylic sp3 C-H and allylic sp3 C-H bonds mediated by DDQ
    Ramesh, D.
    Ramulu, U.
    Rajaram, S.
    Prabhakar, P.
    Venkateswarlu, Y.
    [J]. TETRAHEDRON LETTERS, 2010, 51 (37) : 4898 - 4903
  • [6] Palladium-Catalyzed Allylic Amidation with N-Heterocycles via sp3 C-H Oxidation
    Vemula, Sandeep R.
    Kumar, Dinesh
    Cook, Gregory R.
    [J]. ACS CATALYSIS, 2016, 6 (08): : 5295 - 5301
  • [7] Direct Oxidative Amination of the Methyl C-H Bond in N-Heterocycles over Metal-Free Mesoporous Carbon
    Long, Xiangdong
    Wang, Jia
    Gao, Guang
    Nie, Chao
    Sun, Peng
    Xi, Yongjie
    Li, Fuwei
    [J]. ACS CATALYSIS, 2021, 11 (17): : 10902 - 10912
  • [8] A Catalytic Alkylation of Ketones via sp3 C-H Bond Activation
    Peng, Xue
    Hirao, Yuki
    Yabu, Shunsuke
    Sato, Hirofumi
    Higashi, Masahiro
    Akai, Takuya
    Masaoka, Shigeyuki
    Mitsunuma, Harunobu
    Kanai, Motomu
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (10): : 6333 - 6346
  • [9] Metal-Free Synthesis of N-Heterocycles via Intramolecular Electrochemical C-H Aminations
    Wang, Huiqiao
    Zheng, Yongjun
    Xu, Hucheng
    Zou, Jiaru
    Jin, Congrui
    [J]. FRONTIERS IN CHEMISTRY, 2022, 10
  • [10] Metal-free oxidative synthesis of quinazolinones via dual amination of sp3 C-H bonds
    Zhao, Dan
    Wang, Teng
    Li, Jian-Xin
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (49) : 6471 - 6474