Rhodium(III)-Catalyzed Regioselective C4 Alkylation of Indoles with Nitroalkenes

被引:0
|
作者
Zhao, Ru [1 ]
Lv, Xulin [1 ]
Yang, Hao-Ran [1 ]
Gao, Lijun [1 ]
Zhou, Liming [1 ]
Fang, Shaoming [1 ,2 ]
Liu, Shuang-Liang [1 ]
机构
[1] Zhengzhou Univ Light Ind, Coll Mat & Chem Engn, Zhengzhou 450001, Peoples R China
[2] Zhengzhou Univ Light Ind, Key Lab Surface & Interface Sci & Technol Henan Pr, Zhengzhou 450001, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 23期
基金
中国国家自然科学基金;
关键词
DIRECTING-GROUP; H ACTIVATION; FUNCTIONALIZATION; MALEIMIDES; ARYLATION;
D O I
10.1021/acs.joc.4c02236
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Rh(III)-catalyzed indole C4-H bond addition to nitroalkenes is disclosed under mild and redox-neutral reaction conditions, offering straightforward access to various 4-(2-nitroalkyl)indoles (34 examples) with excellent chemo- and regioselectivity. Furthermore, late-stage diversifications and mechanistic studies were also performed.
引用
收藏
页码:17844 / 17849
页数:6
相关论文
共 50 条
  • [1] Rh(iii)-Catalyzed regioselective C4 alkylation of indoles with allylic alcohols: direct access to β-indolyl ketones
    Pan, Changduo
    Huang, Gao
    Shan, Yujia
    Li, Yiting
    Yu, Jin-Tao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (16) : 3038 - 3042
  • [2] Rhodium(III)-Catalyzed Regioselective Direct C4-Alkylation and C2-Annulation of Indoles: Straightforward Access to Indolopyridone
    Biswas, Aniruddha
    Samanta, Rajarshi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (12) : 1426 - 1436
  • [3] Rhodium(II)-Catalyzed Regioselective Remote C-H Alkylation of Protic Indoles
    Kong, Lingheng
    Han, Xi
    Chen, Haohua
    Sun, Huaming
    Lan, Yu
    Li, Xingwei
    ACS CATALYSIS, 2021, 11 (09) : 4929 - 4935
  • [4] Rhodium(III)-Catalyzed Regioselective C-H Allylation and Prenylation of Indoles at C4-Position
    Zhang, Shang-Shi
    Liu, Yan-Zhi
    Zheng, Yi-Chuan
    Xie, Hui
    Chen, Shao-Yong
    Song, Jia-Lin
    Shu, Bing
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (01) : 64 - 70
  • [5] Palladium-Catalyzed Regioselective C4 Functionalization of Indoles with Quinones
    Aslam, Mohammad
    Devkota, Shreedhar
    Jamshaid, Sana
    Lee, Yong Rok
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (18) : 3179 - 3192
  • [6] Rhodium(III)-Catalyzed Direct C7-Selective Alkenylation and Alkylation of Indoles with Maleimides
    Sheng, Yaoguang
    Gao, Yi
    Duan, Bingbing
    Lv, Mengxia
    Chen, Yao
    Yang, Mengjie
    Zhou, Jianmin
    Liang, Guang
    Song, Zengqiang
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (02) : 307 - 313
  • [7] Rhodium(iii)-catalyzed regioselective C(sp2)-H activation of indoles at the C4-position with iodonium ylides
    Wu, Fuhai
    Xiao, Lin
    Xie, Hui
    Chen, Shao-Yong
    Song, Jia-Lin
    Zheng, Yi-Chuan
    Liu, Yan-Zhi
    Zhang, Shang-Shi
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (25) : 5055 - 5059
  • [8] Rhodium(III)-Catalyzed Direct Regioselective Synthesis of 7-Substituted Indoles
    Song, Zengqiang
    Samanta, Rajarshi
    Antonchick, Andrey P.
    ORGANIC LETTERS, 2013, 15 (22) : 5662 - 5665
  • [9] Rh(iii)-Catalyzed dienylation and cyclopropylation of indoles at the C4 position with alkylidenecyclopropanes
    Liu, Yan-Zhi
    Zeng, Yao-Fu
    Shu, Bing
    Zheng, Yi-Chuan
    Xiao, Lin
    Chen, Shao-Yong
    Song, Jia-Lin
    Zhang, Xuanxuan
    Zhang, Shang-Shi
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (16): : 4287 - 4293
  • [10] Rhodium(III)-Catalyzed Regioselective C-H Alkenylation and Alkylation of Menadione Analogues with β-Trifluoromethyl Enones
    Sindhe, Haritha
    Kumar, Anand
    Gulipelli, Haneesha
    Kamble, Akshay
    Singh, Amardeep
    Sharma, Satyasheel
    ORGANIC LETTERS, 2024, 26 (46) : 10002 - 10007