Cp*Rh(III)-catalyzed C(sp3)-H alkenylation and arylation of 8-methylquinolines with quinones and thiophenes

被引:13
作者
Shan, Baode [1 ]
Miao, Qing [1 ]
Wang, Rui [1 ]
Jia, Guohui [1 ]
Zhao, Huaiqing [1 ]
机构
[1] Univ Jinan, Sch Chem & Chem Engn, Jinan 250022, Shandong, Peoples R China
关键词
Rh(III) catalyst; C(sp(3))-H functionalization; 8-Methylquinolines; Quinones; Thiophenes; C-H BOND; INTERMOLECULAR AMIDATION; FUNCTIONALIZATION;
D O I
10.1016/j.catcom.2019.05.008
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Rh(III)-catalyzed oxidative cross-coupling of C(sp(3))-H bonds with C(sp(2))-H bonds has been accomplished under mild conditions. This method furnishes a streamlined route for the C(sp(3))-H alkenylation and arylation of 8-methylquinolines. This protocol enables 8-methylquinolines to couple with different quinone and thiophene derivatives.
引用
收藏
页数:6
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共 29 条
  • [1] Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups
    Chen, Zhengkai
    Wang, Binjie
    Zhang, Jitan
    Yu, Wenlong
    Liu, Zhanxiang
    Zhang, Yuhong
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09): : 1107 - 1295
  • [2] Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation
    Cho, Seung Hwan
    Kim, Ji Young
    Kwak, Jaesung
    Chang, Sukbok
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 5068 - 5083
  • [3] A highly selective catalytic method for the oxidative functionalization of C-H bonds
    Dick, AR
    Hull, KL
    Sanford, MS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) : 2300 - 2301
  • [4] Dyker G, 2005, HANDBOOK OF C-H TRANSFORMATIONS: APPLICATIONS IN ORGANIC SYNTHESIS, VOL 1, pV
  • [5] 8-Methylquinoline palladacycles: stable and efficient catalysts for carbon-carbon bond formation
    Evans, P
    Hogg, P
    Grigg, R
    Nurnabi, M
    Hinsley, J
    Sridharan, V
    Suganthan, S
    Korn, S
    Collard, S
    Muir, JE
    [J]. TETRAHEDRON, 2005, 61 (41) : 9696 - 9704
  • [6] 3d Transition Metals for C-H Activation
    Gandeepan, Parthasarathy
    Mueller, Thomas
    Zell, Daniel
    Cera, Gianpiero
    Warratz, Svenja
    Ackermann, Lutz
    [J]. CHEMICAL REVIEWS, 2019, 119 (04) : 2192 - 2452
  • [7] Syntheses and Transformations of α-Amino Acids via Palladium-Catalyzed Auxiliary-Directed sp3 C-H Functionalization
    He, Gang
    Wang, Bo
    Nack, William A.
    Chen, Gong
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (04) : 635 - 645
  • [8] Jean M., 2013, STEREOSELECTIVE SYNT, V1, P667
  • [9] Cp*Rh(III)-catalyzed C(sp3)-H alkylation of 8-methylquinolines in aqueous media
    Kim, Saegun
    Han, Sangil
    Park, Jihye
    Sharma, Satyasheel
    Mishra, Neeraj Kumar
    Oh, Hyunjung
    Kwak, Jong Hwan
    Kim, In Su
    [J]. CHEMICAL COMMUNICATIONS, 2017, 53 (21) : 3006 - 3009
  • [10] Rhodium(III)-Catalyzed Alkenylation Reactions of 8-Methylquinolines with Alkynes by C(sp3)-H Activation
    Liu, Bingxian
    Zhou, Tao
    Li, Bin
    Xu, Shansheng
    Song, Haibin
    Wang, Baiquan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (16) : 4191 - 4195