Directed C8-H allylation of quinoline N-oxides with vinylcyclopropanes via sequential C-H/C-C activation

被引:11
|
作者
Mandal, Santu [1 ]
Karjee, Pallab [1 ]
Saha, Sharajit [1 ]
Punniyamurthy, Tharmalingam [1 ]
机构
[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India
关键词
D O I
10.1039/d2cc06646g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The Rh(iii)-catalyzed C8-allylation of quinoline N-oxides has been accomplished using vinylcyclopropanes as an allyl source with excellent diastereoselectivity at room temperature. The C-H/C-C activation, substrate scope and natural product mutation are the important practical features.
引用
收藏
页码:2823 / 2826
页数:4
相关论文
共 50 条
  • [1] CoIII-Catalyzed C-H Alkenylation and Allylation with Cyclopropenes via Sequential C-H/C-C Bond Activation
    Kim, Ye Lim
    Park, Sun-a
    Choi, Seoung-Mi
    Park, Jong-Un
    Kim, Ju Hyun
    [J]. ORGANIC LETTERS, 2021, 23 (17) : 6674 - 6679
  • [2] Rhodium(III)-catalyzed C-H/C-C activation sequence: vinylcyclopropanes as versatile synthons in direct C-H allylation reactions
    Wu, Jia-Qiang
    Qiu, Zhi-Ping
    Zhang, Shang-Shi
    Liu, Jing-Gong
    Lao, Ye-Xing
    Gu, Lian-Quan
    Huang, Zhi-Shu
    Li, Juan
    Wang, Honggen
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (01) : 77 - 80
  • [3] Metal-free C8-H functionalization of quinoline N-oxides with ynamides
    Hu, Weican
    Zhang, Feiyang
    Chen, Chen
    Qi, Tianhang
    Shen, Yanlong
    Qian, Guoying
    Rong, Zhouting
    [J]. CHEMICAL COMMUNICATIONS, 2021, 57 (57) : 6995 - 6998
  • [4] Rh(III)-Catalyzed Selective C8-H Acylmethylation of Quinoline N-Oxides
    You, Chang
    Pi, Chao
    Wu, Yangjie
    Cui, Xiuling
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (21) : 4068 - 4072
  • [5] Manganese-catalyzed allylation via sequential C-H and C-C/C-Het bond activation
    Lu, Qingquan
    Klauck, Felix J. R.
    Glorius, Frank
    [J]. CHEMICAL SCIENCE, 2017, 8 (05) : 3379 - 3383
  • [6] Access to 8-Azachromones via Activation of C-H in N-Oxides
    Wang, Dong
    Feng, Hairong
    Li, Linna
    Liu, Zhenlin
    Yang, Zhongli
    Yu, Peng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (20): : 11275 - 11287
  • [7] Ru-Catalyzed Deoxygenative Regioselective C8-H Arylation of Quinoline N-Oxides
    Kim, Jinwoo
    Kim, Suhyeon
    Kim, Dongwook
    Chang, Sukbok
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (20): : 13150 - 13158
  • [8] Rhodium(III)-Catalyzed Direct C7 Allylation of Indolines via Sequential C-H and C-C Activation
    Wang, Qiuling
    Zhi, Chang-Lei
    Lu, Pei-Pei
    Liu, Shuang
    Zhu, Xinju
    Hao, Xin-Qi
    Song, Mao-Ping
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (06) : 1253 - 1258
  • [9] Cp*Rh(III)-Catalyzed Directed C-H Methylation and Arylation of Quinoline N-Oxides at the C-8 Position
    Wang, Bao
    Li, Chunpu
    Liu, Hong
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (17) : 3029 - 3034
  • [10] Directed C-H Alkenylation of Quinoline N-Oxides at the C-8 Position Using a Cationic Rhodium(I) Catalyst
    Shibata, Takanori
    Matsuo, Yusuke
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) : 1516 - 1520