Rh(iii)-Catalyzed regioselective C4 alkylation of indoles with allylic alcohols: direct access to β-indolyl ketones

被引:20
作者
Pan, Changduo [1 ]
Huang, Gao [2 ]
Shan, Yujia [2 ]
Li, Yiting [2 ]
Yu, Jin-Tao [2 ]
机构
[1] Jiangsu Univ Technol, Sch Chem & Environm Engn, Changzhou 213001, Peoples R China
[2] Changzhou Univ, Jiangsu Key Lab Adv Catalyt Mat & Technol, Sch Petrochem Engn, Changzhou 213164, Peoples R China
基金
中国国家自然科学基金;
关键词
H ACTIVATION; OXIDATIVE ALKYLATION; HECK REACTION; FUNCTIONALIZATION; ALLYLATION; ARYLATION; OLEFINATION; C7-FUNCTIONALIZATION; ALKENYLATION; INDOLINES;
D O I
10.1039/d0ob00396d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Rh(iii)-catalyzed and weak coordination carbonyl guided direct C4 alkylation of indoles with allylic alcohols was developed with excellent regioselectivity. This reaction was conducted under mild conditions, leading to a variety of beta-indolyl ketones with good functional group tolerance in moderate to good yields.
引用
收藏
页码:3038 / 3042
页数:5
相关论文
共 50 条
  • [21] Ruthenium(ii)-catalyzed regioselective direct C4-and C5-diamidation of indoles and mechanistic studies
    Devkota, Shreedhar
    Kim, Suyeon
    Yoo, Seok Yeol
    Mohandoss, Sonaimuthu
    Baik, Mu-Hyun
    Lee, Yong Rok
    CHEMICAL SCIENCE, 2021, 12 (34) : 11427 - 11437
  • [22] Palladium-Catalyzed Direct 2-Alkylation of Indoles by Norbornene-Mediated Regioselective Cascade C-H Activation
    Jiao, Lei
    Bach, Thorsten
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) : 12990 - 12993
  • [23] Regiocontrolled direct C4 and C2-methyl thiolation of indoles under rhodium-catalyzed mild conditions
    Maity, Saurabh
    Karmakar, Ujjwal
    Samanta, Rajarshi
    CHEMICAL COMMUNICATIONS, 2017, 53 (90) : 12197 - 12200
  • [24] Co(III), Rh(III) & Ir(III)-Catalyzed Direct C-H Alkylation/Alkenylation/Arylation with Carbene Precursors
    Nunewar, Saiprasad
    Kumar, Sanjeev
    Talakola, Srilakshmi
    Nanduri, Srinivas
    Kanchupalli, Vinaykumar
    CHEMISTRY-AN ASIAN JOURNAL, 2021, 16 (05) : 443 - 459
  • [25] 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
  • [26] The regioselective annulation of alkylidenecyclopropanes by Rh(iii)-catalyzed C-H/C-C activation to access spirocyclic benzosultams
    Li, Qiuyun
    Yuan, Xin
    Li, Bin
    Wang, Baiquan
    CHEMICAL COMMUNICATIONS, 2020, 56 (12) : 1835 - 1838
  • [27] Iridium-Catalyzed Direct Regioselective C4-Amidation of Indoles under Mild Conditions
    Chen, Shuyou
    Feng, Boya
    Zheng, Xuesong
    Yin, Jiangliang
    Yang, Shiping
    You, Jingsong
    ORGANIC LETTERS, 2017, 19 (10) : 2502 - 2505
  • [28] Rhodium(III-Catalyzed C8-Selective C-H Alkenylation and Alkylation of 1, 2, 3, 4-Tetrahydroquinolines with Styrenes and Allylic Alcohols
    Yang, Ji
    Chen, Changjun
    Zhao, Haoqiang
    Li, Bohan
    He, Zhenni
    Xu, Lijin
    Shi, Qian
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (07) : 1027 - 1035
  • [29] Allylic Acetal as 3C Synthon in Rh(III)-Catalyzed Divergent C-H Activation/[4+3] Annulation: Easy Access to Benzodiazepines
    Hu, Mingming
    Pi, Chao
    Wu, Yangjie
    Cui, Xiuling
    ORGANIC LETTERS, 2025,
  • [30] C6-Selective Direct Alkylation of Pyridones with Diazo Compounds under Rh(III)-Catalyzed Mild Conditions
    Das, Debapratim
    Biswas, Aniruddha
    Karmakar, Ujjwal
    Chand, Santanu
    Samanta, Rajarshi
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (03) : 842 - 848