Ligand-Accelerated Palladium(II)-Catalyzed Enantioselective Amination of C(sp2)-H Bonds

被引:20
作者
Cheng, Xiu-Fen [1 ,2 ,3 ]
Fei, Fan [1 ,2 ]
Li, Yan [1 ,2 ]
Hou, Yi-Ming [1 ,2 ]
Zhou, Xin [1 ,2 ]
Wang, Xi-Sheng [1 ,2 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
[3] Shandong Normal Univ, Coll Chem Chem Engn & Mat Sci, Collaborat Innovat Ctr Functionalized Probes Chem, Key Lab Mol & Nano Probes,Minist Educ,Shandong Pr, Jinan 250014, Peoples R China
基金
美国国家科学基金会; 中国博士后科学基金;
关键词
C-H AMINATION; NITROGEN-ATOM TRANSFER; INDOLE ALKALOIDS; CYTOTOXIC ACTIVITY; C(SP(3))-H BONDS; TERMINAL OLEFINS; SULFAMATE ESTERS; ACTIVATION; AMIDATION; DIRHODIUM(II);
D O I
10.1021/acs.orglett.0c02216
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first example of the Pd(II)-catalyzed enantioselective amination of aryl C-H bonds is reported. The key to the successful realization of this asymmetric catalytic transformation was the identification of mono-N-protected alpha-amino-O-methylhydroxamic acid (MPAHA) ligands, which promote reactivity under mild conditions and control enantioselectivity. The counteranions in the solvent medium, hexafluoroacetylacetate and acetate, were also found to play key roles in stereocontrol and reactivity enhancement.
引用
收藏
页码:6394 / 6398
页数:5
相关论文
共 72 条
  • [1] Ligand-assisted, copper-catalyzed enantioselective benzylic amination
    Barman, Dipti N.
    Nicholas, Kenneth M.
    [J]. TETRAHEDRON LETTERS, 2010, 51 (14) : 1815 - 1818
  • [2] Structural requirements of bitter taste receptor activation
    Brockhoff, Anne
    Behrens, Maik
    Niv, Masha Y.
    Meyerhof, Wolfgang
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (24) : 11110 - 11115
  • [3] Pericyclic Cascade with Chirality Transfer: Reaction Pathway and Origin of Enantioselectivity of the Hetero-Claisen Approach to Oxindoles
    Celebi-Oelcuem, Nihan
    Lam, Yu-hong
    Richmond, Edward
    Ling, Kenneth B.
    Smith, Andrew D.
    Houk, Kendall N.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (48) : 11478 - 11482
  • [4] Clark J. S., 2005, J AM CHEM SOC, P5175
  • [5] Catalytic C-H amination: the stereoselectivity issue
    Collet, Florence
    Lescot, Camille
    Dauban, Philippe
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) : 1926 - 1936
  • [6] Studies in catalytic C-H amination involving nitrene C-H insertion
    Collet, Florence
    Lescot, Camille
    Liang, Chungen
    Dauban, Philippe
    [J]. DALTON TRANSACTIONS, 2010, 39 (43) : 10401 - 10413
  • [7] Catalytic C-H amination: recent progress and future directions
    Collet, Florence
    Dodd, Robert H.
    Dauban, Philippe
    [J]. CHEMICAL COMMUNICATIONS, 2009, (34) : 5061 - 5074
  • [8] Asymmetric Synthesis of Amines through Rhodium-Catalyzed C-H Amination with Sulfonimidoylnitrenes
    Darses, Benjamin
    Jarvis, Amanda G.
    Mafroud, Abdel-Kader
    Estenne-Bouhtou, Genevieve
    Dargazanli, Gihad
    Dauban, Philippe
    [J]. SYNTHESIS-STUTTGART, 2013, 45 (15): : 2079 - 2087
  • [9] Nitrene Chemistry in Organic Synthesis: Still in Its Infancy?
    Dequirez, Geoffroy
    Pons, Valerie
    Dauban, Philippe
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (30) : 7384 - 7395
  • [10] Generation of Heteroatom Stereocenters by Enantioselective C-H Functionalization
    Diesel, Johannes
    Cramer, Nicolai
    [J]. ACS CATALYSIS, 2019, 9 (10) : 9164 - 9177