Rh(III)-Catalyzed Double C-H Functionalization of Indoles with Cyclopropenones via Sequential C-H/C-C/C-H Bond Activation

被引:15
|
作者
Zhang, Yan-Bo [1 ]
Li, Bin-Shi [1 ]
Xu, Guo-Jie [1 ]
Sun, Wei [1 ]
Sun, Meng [1 ]
机构
[1] Northwest Univ, Coll Chem & Mat Sci, Key Lab Synthet & Nat Funct Mol, Minist Educ, Xian 710127, Peoples R China
基金
中国国家自然科学基金;
关键词
5+1 ANNULATION REACTION; HETEROCYCLES; STRATEGIES; CATALYSIS; ACCESS; ARENES;
D O I
10.1021/acs.orglett.3c01292
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Anunprecedented Rh-(III)-catalyzed double C-H functionalizationof indoles with cyclopropenones via sequential C-H/C-C/C-Hbond activation has been developed. This procedure represents thefirst example for assembling of cyclopenta-[b]-indolesutilizing cyclopropenones as 3C synthons. This powerful approach showsexcellent chemo- and regioselectivity, wide functional group tolerance,and good reaction yields.
引用
收藏
页码:3922 / 3926
页数:5
相关论文
共 50 条
  • [21] Oxygenation via C-H/C-C Bond Activation with Molecular Oxygen
    Liang, Yu-Feng
    Jiao, Ning
    ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (07) : 1640 - 1653
  • [22] Recent Advances on Copper-Catalyzed C-C Bond Formation via C-H Functionalization
    Almasalma, Ahmad A.
    Mejia, Esteban
    SYNTHESIS-STUTTGART, 2020, 52 (18): : 2613 - 2622
  • [23] Rh(III)- and Ir(III)-Catalyzed C-C Bond Cross Couplings from C-H Bonds
    Wencel-Delord, Joanna
    Patureau, Frederic W.
    Glorius, Frank
    C-H BOND ACTIVATION AND CATALYTIC FUNCTIONALIZATION I, 2016, 55 : 1 - 27
  • [24] 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
    CHEMICAL COMMUNICATIONS, 2015, 51 (01) : 77 - 80
  • [25] Expedient C-H allylation of sulfoxonium ylides: merging C-H and C-C/C-het bond activation
    Saha, Sharajit
    Bhattacharyya, Hemanga
    Karjee, Pallab
    Debnath, Bijoy
    Verma, Kshitiz
    Punniyamurthy, Tharmalingam
    CHEMICAL COMMUNICATIONS, 2023, 59 (95) : 14173 - 14176
  • [26] Rhodium-catalyzed C-C coupling reactions via double C-H activation
    Li, Shuai-Shuai
    Qin, Liu
    Dong, Lin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (20) : 4554 - 4570
  • [27] Biorelevant Weakly Coordinating Directing Group Assisted C-H Alkenylation with Cyclopropanols via Sequential C-H/C-C Activation
    Paul, Tripti
    Basak, Shubhajit
    Nanjegowda, Maniya V.
    Punniyamurthy, Tharmalingam
    ORGANIC LETTERS, 2023, 25 (50) : 8975 - 8980
  • [28] Ruthenium-catalyzed C-H activation and C-C bond formation.
    Gunnoe, TB
    Lail, M
    Arrowood, BN
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U58 - U58
  • [29] 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
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (06) : 1253 - 1258
  • [30] ANISTROPY OF C-H AND C-C BOND POLARIZABILITIES
    MURRELL, JN
    MUSGRAVE, MJ
    TRANSACTIONS OF THE FARADAY SOCIETY, 1967, 63 (540P): : 2849 - &