Atroposelective Synthesis of Axially Chiral C2-Arylindoles via Rhodium-Catalyzed Asymmetric C-H Bond Insertion

被引：19
|
作者：
Liu, Junheng [1 ]
Li, Qiongya [1 ]
Shao, Ying [1 ]
Sun, Jiangtao [1 ]
机构：
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat Technol, Changzhou 213164, Jiangsu, Peoples R China
来源：
ORGANIC LETTERS | 2022年 / 24卷 / 25期
关键词：
ENANTIOSELECTIVE SYNTHESIS; NATURAL-PRODUCTS; ATROPISOMERS; CONSTRUCTION; ARYLATION; INDOLES; ACCESS;
D O I：
10.1021/acs.orglett.2c01818
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly efficient rhodium-catalyzed formal C-H insertion reaction between indoles and 1-diazonaphthoquinones has been established, providing a novel protocol for the atroposelective synthesis of axially chiral C2-arylindoles (up to 99:1 er) under mild reaction conditions. Typically, only 1 mol % of Rh-2(S-PTTL)(4) is used and the chelation group is not needed for this conversion.
引用
收藏
页码：4670 / 4674
页数：5
相关论文
共 50 条
  • [1] Atroposelective Synthesis of N-N Axially Chiral Bipyrroles via Rhodium-Catalyzed C-H Insertion Reaction
    Wang, Changkai
    Sun, Jiangtao
    [J]. ORGANIC LETTERS, 2023, 25 (26) : 4808 - 4812
  • [2] Rhodium-Catalyzed Atroposelective C-H Arylation: Efficient Synthesis of Axially Chiral Heterobiaryls
    Wang, Qiang
    Cai, Zhong-Jian
    Liu, Chen-Xu
    Gu, Qing
    You, Shu-Li
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (24) : 9504 - 9510
  • [3] Rhodium-Catalyzed Atroposelective Access to Axially Chiral Olefins via C-H Bond Activation and Directing Group Migration
    Mi, Ruijie
    Chen, Haohua
    Zhou, Xukai
    Li, Nan
    Ji, Danqing
    Wang, Fen
    Lan, Yu
    Li, Xingwei
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (01)
  • [4] Rhodium-Catalyzed Atroposelective Construction of Indoles via C-H Bond Activation
    Sun, Lincong
    Chen, Haohua
    Liu, Bingxian
    Chang, Junbiao
    Kong, Lingheng
    Wang, Fen
    Lan, Yu
    Li, Xingwei
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (15) : 8391 - 8395
  • [5] Atroposelective Synthesis of Axially Chiral Styrenes via an Asymmetric C-H Functionalization Strategy
    Jin, Liang
    Yao, Qi-Jun
    Xie, Pei-Pei
    Li, Ya
    Zhan, Bei-Bei
    Han, Ye-Qiang
    Hong, Xin
    Shi, Bing-Feng
    [J]. CHEM, 2020, 6 (02): : 497 - 511
  • [6] Rhodium(III)-Catalyzed Atroposelective Synthesis of C-N Axially Chiral Naphthylamines and Variants via C-H Activation
    Wang, Peiyuan
    Huang, Yaling
    Jing, Jierui
    Wang, Fen
    Li, Xingwei
    [J]. ORGANIC LETTERS, 2022, 24 (13) : 2531 - 2535
  • [7] Rhodium-catalyzed atroposelective access to trisubstituted olefins via C-H bond olefination of diverse arenes
    Zhu, Xiaohan
    Mi, Ruijie
    Yin, Jie
    Wang, Fen
    Li, Xingwei
    [J]. CHEMICAL SCIENCE, 2023, 14 (29) : 7999 - 8005
  • [8] Rhodium-Catalyzed Regioselective Ortho C-H Olefination of 2-Arylindoles via NH-Indole-Directed C-H Bond Cleavage
    Han, Qingshuai
    Guo, Xiemin
    Tang, Ziyuan
    Su, Lv
    Yao, Zizhu
    Zhang, Xiaofeng
    Lin, Shen
    Xiang, Shengchang
    Huang, Qiufeng
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (05) : 972 - 984
  • [9] Diastereoselective synthesis of tetrahydropyridines via rhodium-catalyzed C-H bond activation
    Lu, Colin
    Duttwyler, Simon
    Ellman, Jonathan
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [10] Multicomponent Synthesis of Iminocoumarins via Rhodium-Catalyzed C-H Bond Activation
    Chen, Zhan
    Jin, Shengnan
    Jiang, Wenyao
    Zhu, Feimin
    Chen, Yuqi
    Zhao, Yingwei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (16): : 11006 - 11013
12345