Imidate as the Intact Directing Group for the Cobalt-Catalyzed C-H Allylation

被引:25
|
作者
Tanaka, Ryo [1 ]
Tanimoto, Iku [1 ]
Kojima, Masahiro [1 ]
Yoshino, Tatsuhiko [1 ]
Matsunaga, Shigeki [1 ]
机构
[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
来源
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 20期
关键词
ACTIVATION; FUNCTIONALIZATION; ISOQUINOLINES; ACCESS; COUPLING/CYCLIZATION; 1H-INDAZOLES; QUINAZOLINES; CYCLIZATION; AMIDATION; OLEFINS;
D O I
10.1021/acs.joc.9b01972
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cobalt-catalyzed C-H allylation reactions of NH-free benzimidate using vinylcyclopropanes or allyl carbonate are reported. The reactive and relatively unstable imidate groups remain intact during the C-H allylations to afford functionalized imidates without dealcoholizations. The thus obtained allylated imidate was subsequently converted into other heterocyclic structures through a following C-H functionalization reaction, demonstrating the synthetic utility of this method.
引用
收藏
页码:13203 / 13210
页数:8
相关论文
共 50 条
  • [31] Current Mechanistic Understanding of Cobalt-Catalyzed C-H Functionalization
    Planas, Oriol
    Chirila, Paula G.
    Whiteoak, Christopher J.
    Ribas, Xavi
    ADVANCES IN ORGANOMETALLIC CHEMISTRY, VOL 69, 2018, 69 : 209 - 282
  • [32] Cobalt-catalyzed C-H olefination of aromatics with unactivated alkenes
    Manoharan, Ramasamy
    Sivakumar, Ganesan
    Jeganmohan, Masilamani
    CHEMICAL COMMUNICATIONS, 2016, 52 (69) : 10533 - 10536
  • [33] Electrochemical Cobalt-Catalyzed C-H Oxygenation at Room Temperature
    Ackermann, Lutz (Lutz.Ackermann@chemie.uni-goettingen.de), 1600, American Chemical Society (139):
  • [34] Cobalt-catalyzed C-H methylation for late stage functionalization
    Friis, Stig
    Ackermann, Lutz
    Johansson, Magnus
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [35] Expedient Cobalt-Catalyzed C-H Alkynylation of (Enantiopure) Benzylamines
    Landge, Vinod G.
    Midya, Siba P.
    Rana, Jagannath
    Shinde, Dinesh R.
    Balaraman, Ekambaram
    ORGANIC LETTERS, 2016, 18 (20) : 5252 - 5255
  • [36] Cobalt-Catalyzed Oxidative C-H Activation: Strategies and Concepts
    Mei, Ruhuai
    Dhawa, Uttam
    Samanta, Ramesh C.
    Ma, Wenbo
    Wencel-Delord, Joanna
    Ackermann, Lutz
    CHEMSUSCHEM, 2020, 13 (13) : 3306 - 3356
  • [37] Cobalt-catalyzed intramolecular C-H amination with arylsulfonyl azides
    Ruppel, Joshua V.
    Kamble, Rajesh M.
    Zhang, X. Peter
    ORGANIC LETTERS, 2007, 9 (23) : 4889 - 4892
  • [38] Electrochemical Cobalt-Catalyzed C-H Oxygenation at Room Temperature
    Sauermann, Nicolas
    Meyer, Tjark H.
    Tian, Cong
    Ackermann, Lutz
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (51) : 18452 - 18455
  • [39] Rhodium and cobalt-catalyzed functionalization of formyl C-H bonds
    Dong, Vy Maria
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [40] Cobalt(II)-catalyzed C-H functionalization using an N,N′-bidentate directing group
    Kommagalla, Yadagiri
    Chatani, Naoto
    COORDINATION CHEMISTRY REVIEWS, 2017, 350 : 117 - 135