Visible-Light-Promoted Asymmetric Cross-Dehydrogenative Coupling of Tertiary Amines to Ketones by Synergistic Multiple Catalysis

被引：222
作者：
Yang, Qi [1 ,2 ]
Zhang, Long [1 ,2 ]
Ye, Chen [3 ]
Luo, Sanzhong [1 ,2 ]
Wu, Li-Zhu [3 ]
Tung, Chen-Ho [3 ]
机构：
[1] Chinese Acad Sci, Inst Chem, Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Chinese Acad Sci, Key Lab Photochem Convers & Optoelect Mat, Tech Inst Phys & Chem, Beijing 100190, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 13期
关键词：
amines; cross-coupling; hydrogen; photochemistry; reaction mechanisms; C-H BONDS; MERGING PHOTOREDOX CATALYSIS; DUAL CATALYSIS; BETA-KETOCARBONYLS; MOLECULAR-OXYGEN; COMBINING PHOTOREDOX; ACID; ACTIVATION; CASCADE; ALKYLATION;
D O I：
10.1002/anie.201700572
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Reported herein is an unprecedented photocatalytic asymmetric cross-dehydrogenative coupling reaction between tertiary amines and simple ketones, and it proceeds by synergistic multiple catalysis with substoichiometric amounts of a hydrogen acceptor. This process is enabled by a simple chiral primary amine catalyst through the coupling of a catalytic enamine intermediate and an iminium cation intermediate in situ generated from tetrahydroisoquinoline derivatives by coupled Ru/Co catalysis.
引用
收藏
页码：3694 / 3698
页数：5
相关论文
共 77 条
  • [1] Synergistic catalysis: A powerful synthetic strategy for new reaction development
    Allen, Anna E.
    MacMillan, David W. C.
    [J]. CHEMICAL SCIENCE, 2012, 3 (03) : 633 - 658
  • [2] [Anonymous], ANGEW CHEM, DOI DOI 10.1038/NCHEM.1452
  • [3] [Anonymous], 2012, ANGEW CHEM INT EDIT
  • [4] The Photocatalyzed Aza-Henry Reaction of N-Aryltetrahydroisoquinolines: Comprehensive Mechanism, H•-versus H+-Abstraction, and Background Reactions
    Bartling, Hanna
    Eisenhofer, Anna
    Koenig, Burkhard
    Gschwind, Ruth M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (36) : 11860 - 11871
  • [5] Bergonzini G, 2014, CHEM SCI, V5, P112, DOI [10.1039/c3sc52265b, 10.1039/C3SC52265B]
  • [6] Brimioulle R., 2015, Angew. Chem, V127, P3944
  • [7] Enantioselective Catalysis of Photochemical Reactions
    Brimioulle, Richard
    Lenhart, Dominik
    Maturi, Mark M.
    Bach, Thorsten
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (13) : 3872 - 3890
  • [8] Catalytic asymmetric cross-dehydrogenative coupling: activation of C-H bonds by a cooperative bimetallic catalyst system
    Cao, Weidi
    Liu, Xiaohua
    Peng, Ruixue
    He, Peng
    Lin, Lili
    Feng, Xiaoming
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (33) : 3470 - 3472
  • [9] Visible-Light-Promoted Stereoselective Alkylation by Combining Heterogeneous Photocatalysis with Organocatalysis
    Cherevatskaya, Maria
    Neumann, Matthias
    Fueldner, Stefan
    Harlander, Christoph
    Kuemmel, Susanne
    Dankesreiter, Stephan
    Pfitzner, Arno
    Zeitler, Kirsten
    Koenig, Burkhard
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (17) : 4062 - 4066
  • [10] Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C-H Functionalization
    Condie, Allison G.
    Gonzalez-Gomez, Jose C.
    Stephenson, Corey R. J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) : 1464 - +
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