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 78 条
  • [1] Direct Selective Oxidative Cross-Coupling of Simple Alkanes with Heteroarenes
    Antonchick, Andrey P.
    Burgmann, Lars
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (11) : 3267 - 3271
  • [2] US FDA Approved Drugs from 2015-June 2020: A Perspective
    Bhutani, Priyadeep
    Joshi, Gaurav
    Raja, Nivethitha
    Bachhav, Namrata
    Rajanna, Prabhakar K.
    Bhutani, Hemant
    Paul, Atish T.
    Kumar, Raj
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2021, 64 (05) : 2339 - 2381
  • [3] Synthesis of Pyridine and Dihydropyridine Derivatives by Regio- and Stereoselective Addition to N-Activated Pyridines
    Bull, James A.
    Mousseau, James J.
    Pelletier, Guillaume
    Charette, Andre B.
    [J]. CHEMICAL REVIEWS, 2012, 112 (05) : 2642 - 2713
  • [4] Catalytic Enantioselective Addition of Prochiral Radicals to Vinylpyridines
    Cao, Kangning
    Tan, Siu Min
    Lee, Richmond
    Yang, Songwei
    Jia, Hongshao
    Zhao, Xiaowei
    Qiao, Baokun
    Jiang, Zhiyong
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (13) : 5437 - 5443
  • [5] Catalytic Asymmetric 1,4-Reduction of α-Branched 2-Vinyl-azaarenes by a Chiral SPINOL-Derived Borophosphate
    Cao, Yang
    Zhang, Shouqi
    Antilla, Jon C.
    [J]. ACS CATALYSIS, 2020, 10 (19): : 10914 - 10919
  • [6] Metal-complexes of optically active amino- and imino-based pyridine ligands in asymmetric catalysis
    Chelucci, Giorgio
    [J]. COORDINATION CHEMISTRY REVIEWS, 2013, 257 (11-12) : 1887 - 1932
  • [7] Modular Synthesis of Enantioenriched 1,1,2-Triarylethanes by an Enantioselective Arylboration and Cross-Coupling Sequence
    Chen, Bin
    Cao, Peng
    Yin, Xuemei
    Liao, Yang
    Jiang, Liyin
    Ye, Jialin
    Wang, Min
    Liao, Jian
    [J]. ACS CATALYSIS, 2017, 7 (04): : 2425 - 2429
  • [8] Enantioselective Twofold C-H Annulation of Formamides and Alkynes without Built-in Chelating Groups
    Chen, Hao
    Wang, Yin-Xia
    Luan, Yu-Xin
    Ye, Mengchun
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (24) : 9428 - 9432
  • [9] Hydrogen Atom Transfer Driven Enantioselective Minisci Reaction of Alcohols
    Colgan, Avene C.
    Proctor, Rupert S. J.
    Gibson, David C.
    Chuentragool, Padon
    Lahdenpera, Antti S. K.
    Ermanis, Kristaps
    Phipps, Robert J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (25)
  • [10] Design, Synthesis, and Evaluation of a Helicenoidal DMAP Lewis Base Catalyst
    Crittall, Matthew R.
    Rzepa, Henry S.
    Carbery, David R.
    [J]. ORGANIC LETTERS, 2011, 13 (05) : 1250 - 1253