Cobalt-catalyzed asymmetric hydroboration of aryl ketones with pinacolborane

被引：125
作者：
Guo, Jun [1 ]
Chen, Jianhui [1 ]
Lu, Zhan [1 ]
机构：
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 26期
基金：
美国国家科学基金会;
关键词：
ENANTIOSELECTIVE BOROHYDRIDE REDUCTION; ALKENE HYDROBORATION; HYDROSILYLATION; IRON; CARBONYL; HYDROGENATION; COMPLEXES; ALKYNES; BORANE; CHEMO;
D O I：
10.1039/c5cc01084e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The highly enantioselective cobalt-catalyzed hydroboration reaction of aryl ketones with HBpin was developed using iminopyridine oxazoline ligands. Halides, amines, ethers, sulfides, esters and amides are well tolerated under the mild reaction conditions, demonstrating its synthetic advantage. Substituted diaryl ketones could also be hydroborated with high enantioselectivity.
引用
收藏
页码：5725 / 5727
页数：3
相关论文
共 66 条
  • [51] An Opportunity for Mg-Catalyzed Grignard-Type Reactions: Direct Coupling of Benzylic Halides with Pinacolborane with 10 mol % of Magnesium
    Pintaric, Christine
    Olivero, Sandra
    Gimbert, Yves
    Chavant, Pierre Y.
    Dunach, Elisabet
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (34) : 11825 - 11827
  • [52] Alkoxide-Catalyzed Reduction of Ketones with Pinacolborane
    Query, Ian P.
    Squier, Phillip A.
    Larson, Emily M.
    Isley, Nicholas A.
    Clark, Timothy B.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (15) : 6452 - 6456
  • [53] Recent advances in the asymmetric hydrosilylation of ketones, imines and electrophilic double bonds
    Riant, O
    Mostefaï, N
    Courmarcel, J
    [J]. SYNTHESIS-STUTTGART, 2004, (18): : 2943 - 2958
  • [54] Cobalt Alkyl Complexes of a New Family of Chiral 1,3-Bis(2-pyridylimino)isoindolates and Their Application in Asymmetric Hydrosilylation
    Sauer, Desiree C.
    Wadepohl, Hubert
    Gade, Lutz H.
    [J]. INORGANIC CHEMISTRY, 2012, 51 (23) : 12948 - 12958
  • [55] SINGH VK, 1992, SYNTHESIS-STUTTGART, P605
  • [56] MILD AND STEREOSELECTIVE HYDROBORATIONS OF FUNCTIONALIZED ALKYNES AND ALKENES USING PINACOLBORANE
    TUCKER, CE
    DAVIDSON, J
    KNOCHEL, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) : 3482 - 3485
  • [57] ASYMMETRIC SYNTHESES WITH CHIRAL OXAZABOROLIDINES
    WALLBAUM, S
    MARTENS, J
    [J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (12) : 1475 - 1504
  • [58] Functionalization of alkanes by isolated transition metal boryl complexes
    Waltz, KM
    Hartwig, JF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) : 11358 - 11369
  • [59] Iron-Catalyzed 1,4-Hydroboration of 1,3-Dienes
    Wu, Jessica Y.
    Moreau, Benoit
    Ritter, Tobias
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (36) : 12915 - +
  • [60] Enantioselective borohydride reduction catalyzed by optically active cobalt complexes
    Yamada, T
    Nagata, T
    Sugi, KD
    Yorozu, K
    Ikeno, T
    Ohtsuka, Y
    Miyazaki, D
    Mukaiyama, T
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (18) : 4485 - 4509
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