Enantioselective C2-H Alkylation of Pyridines with 1,3-Dienes via Ni-Al Bimetallic Catalysis

被引:46
|
作者
Li, Jiang-Fei [1 ,2 ]
Pan, Deng [3 ,4 ]
Wang, Hao-Rui [1 ,2 ]
Zhang, Tao [1 ,2 ]
Li, Yi [1 ,2 ]
Huang, Genping [3 ,4 ]
Ye, Mengchun [1 ,2 ,5 ]
机构
[1] Nankai Univ, Coll Chem, Frontiers Sci Ctr New Organ Matter, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Inst Elementoorgan Chem, Coll Chem, Frontiers Sci Ctr New Organ Matter, Tianjin 300071, Peoples R China
[3] Tianjin Univ, Sch Sci, Dept Chem, Tianjin 300072, Peoples R China
[4] Tianjin Univ, Tianjin Key Lab Mol Optoelect Sci, Tianjin 300072, Peoples R China
[5] Haihe Lab Sustainable Chem Transformat, Tianjin 300192, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H BOND; SELECTIVE ALKENYLATION; KINETIC RESOLUTION; ACTIVATION; METAL; FUNCTIONALIZATION; HYDROHETEROARYLATION; SUBSTITUTIONS; HETEROCYCLES; COMBINATION;
D O I
10.1021/jacs.2c09306
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A chiral phosphine oxide-ligated Ni-Al bimetallic catalyst was used to realize an enantioselective C2-H alkylation of pyridines without the need of a C2-block. A wide range of pyridines, including unsubstituted pyridine, C3, C4, and C2-substituted pyridines, and even complex pyridine-containing bioactive molecules are well compatible with the reaction, providing up to 81% yield and up to 97% ee.
引用
收藏
页码:18810 / 18816
页数:7
相关论文
共 50 条
  • [21] A SIMPLE REGIOSPECIFIC SYNTHESIS OF SUBSTITUTED PYRIDINES FROM 2-AZA 1,3-DIENES
    BARLUENGA, J
    JOGLAR, J
    GONZALEZ, FJ
    GOTOR, V
    FUSTERO, S
    JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (25): : 5960 - 5963
  • [22] Bifunctional NHC-Promoted C2-Alkylation of Pyridine via Ni-Al Bimetallic-Catalyzed Hydroarylation of Unactivated Alkenes
    Jiang, Binyang
    Liu, Jia-Ming
    Shi, Shi-Liang
    ACS CATALYSIS, 2023, 13 (09) : 6068 - 6075
  • [23] Bifunctional NHC-Promoted C2-Alkylation of Pyridine via Ni-Al Bimetallic-Catalyzed Hydroarylation of Unactivated Alkenes
    Jiang, Binyang
    Liu, Jia-Ming
    Shi, Shi-Liang
    ACS CATALYSIS, 2023, : 6068 - 6075
  • [24] Ligand-Enabled Ni-Al Bimetallic Catalysis for Nonchelated Dual C-H Annulation of Arylformamides and Alkynes
    Wang, Yin-Xia
    Zhang, Feng-Ping
    Luan, Yu-Xin
    Ye, Mengchun
    ORGANIC LETTERS, 2020, 22 (06) : 2230 - 2234
  • [25] Accessing 1,3-Dienes via Palladium-Catalyzed Allylic Alkylation of Pronucleophiles with Skipped Enynes
    Gao, Shang
    Liu, Hao
    Yang, Chi
    Fu, Zhiyuan
    Yao, Hequan
    Lin, Aijun
    ORGANIC LETTERS, 2017, 19 (18) : 4710 - 4713
  • [26] SYNTHESIS OF 2(E),4(E)-DIENAMIDES AND 2(E),4(E)-DIENOATES FROM 1,3-DIENES VIA 2-PHENYLSULFONYL 1,3-DIENES
    PLOBECK, NA
    BACKVALL, JE
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (14): : 4508 - 4512
  • [27] Ligand-Enabled Ni-Catalyzed Enantioselective Hydroarylation of Styrenes and 1,3-Dienes with Arylboronic Acids
    Lv, Xin-Yang
    Fan, Chao
    Xiao, Li-Jun
    Xie, Jian-Hua
    Zhou, Qi-Lin
    CCS CHEMISTRY, 2019, 1 (04): : 328 - 334
  • [28] C-H Functionalization of Arenes via NHC-Supported Ni/Al Bimetallic Catalysis
    Jiang, Binyang
    Shi, Shi-Liang
    SYNTHESIS-STUTTGART, 2023, 55 (24): : 4049 - 4061
  • [29] Ni-Catalyzed Enantioselective Intermolecular Hydroamination of Branched 1,3-Dienes Using Primary Aliphatic Amines
    Tran, Gael
    Shao, Wen
    Mazet, Clement
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (37) : 14814 - 14822
  • [30] Alkyne dimerization-hydroarylation to form pentasubstituted 1,3-dienes via binuclear nickel catalysis
    Chen, Ke
    Zhu, Hongdan
    Jiang, Shuxin
    Ding, Kuiling
    Peng, Qian
    Wang, Xiaoming
    NATURE COMMUNICATIONS, 2025, 16 (01)