Manganese-Catalyzed Hydrocarbofunctionalization of Internal Alkenes

被引:25
作者
Wang, Dongping [1 ]
He, Yijie [1 ]
Dai, Haotian [1 ]
Huang, Congcong [2 ]
Yuan, Xiang-Ai [2 ]
Xie, Jin [1 ]
机构
[1] Nanjing Univ, State Key Lab Coordinat Chem, Jiangsu Key Lab Adv Organ Mat, Chem & Biomed Innovat Ctr ChemBIC,Sch Chem & Chem, Nanjing 210023, Jiangsu, Peoples R China
[2] Qufu Normal Univ, Sch Chem & Chem Engn, Qufu 273165, Shandong, Peoples R China
基金
中国国家自然科学基金;
关键词
Alkene; Selectivity; Arylation; Alkenylation; Manganese; C-H ACTIVATION; UNACTIVATED ALKENES; SELECTIVE HYDROARYLATION; ASYMMETRIC 1,4-ADDITION; CARBONYL-COMPOUNDS; KETONES; ACIDS; GOLD; ARYL;
D O I
10.1002/cjoc.202000376
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The Summary of main observation and conclusion A highly regio- and chemo-selective dimeric Mn(I)-catalyzed hydroarylation and hydroalkenylation of unbiased internal alkenes with commercially abundant organoboron compounds is reported. A wide range of densely functionalized aliphatic alkenyl amides can successfully undergo site-exclusive hydrocarbofunctionalization in air atmosphere without any exogenous directing auxiliary, affording an enhanced lead library of structurally diverse gamma-functionalized carboxylic acid derivatives in moderate to good yields. The precise chemoselectivity of the reaction among multiple alkene units even in the presence of reactive terminal alkenes highlights the unique catalytic features of manganese catalyst, and the excellent functional group compatibility of primary amides further complements other transition metals.
引用
收藏
页码:1497 / 1502
页数:6
相关论文
共 60 条
  • [1] Kinetic Data for the Transmetalation/Reductive Elimination in Palladium-Catalyzed Suzuki-Miyaura Reactions: Unexpected Triple Role of Hydroxide Ions Used as Base
    Amatore, Christian
    Jutand, Anny
    Le Duc, Gaetan
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (08) : 2492 - 2503
  • [2] Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]
  • [3] Manganese-Catalyzed Hydrofunctionalization of Alkenes
    Carney, Jonathan R.
    Dillon, Barry R.
    Campbell, Leonie
    Thomas, Stephen P.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (33) : 10620 - 10624
  • [4] Recent Advances of Manganese Catalysis for Organic Synthesis
    Carney, Jonathan R.
    Dillon, Barry. R.
    Thomas, Stephen P.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (23) : 3912 - 3929
  • [5] Distinguishing Between Pathways for Transmetalation in Suzuki-Miyaura Reactions
    Carrow, Brad P.
    Hartwig, John F.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (07) : 2116 - 2119
  • [6] Recent Advances in Hydrometallation of Alkenes and Alkynes via the First Row Transition Metal Catalysis
    Chen, Jianhui
    Guo, Jun
    Lu, Zhan
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (11) : 1075 - 1109
  • [7] Manganese(I)-Catalyzed Regio- and Stereoselective 1,2-Diheteroarylation of Allenes: Combination of C-H Activation and Smiles Rearrangement
    Chen, Shi-Yong
    Han, Xiang-Lei
    Wu, Jia-Qiang
    Li, Qingjiang
    Chen, Yunyun
    Wang, Honggen
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (33) : 9939 - 9943
  • [8] Nickel-catalyzed Enantioselective Hydroarylation and Hydroalkenylation of Styrenes
    Chen, Yue-Gang
    Shuai, Bin
    Xu, Xue-Tao
    Li, Yi-Qian
    Yang, Qi-Liang
    Qiu, Hui
    Zhang, Kun
    Fang, Ping
    Mei, Tian-Sheng
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (08) : 3395 - 3399
  • [9] Corey E. J., 1989, The Logic of Chemical Synthesis
  • [10] Nickel-Catalyzed 1,2-Diarylation of Alkenyl Carboxylates: A Gateway to 1,2,3-Trifunctionalized Building Blocks
    Derosa, Joseph
    Kang, Taeho
    Tran, Van T.
    Wisniewski, Steven R.
    Karunananda, Malkanthi K.
    Jankins, Tanner C.
    Xu, Kane L.
    Engle, Keary M.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (03) : 1201 - 1205