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

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 21期

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

页码：3922 / 3926

页数：5

共 50 条

[41] Sequential hydrocarbon functionalization: Allylic C-H oxidation/vinylic C-H arylation
Delcamp, Jared H.
White, M. Christina
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (47) : 15076 - 15077
[42] Divergent Coupling of Benzocyclobutenones with Indoles via C-H and C-C Activations
Lu, Hong
Zhao, Tian-Tian
Bai, Jin-Hua
Ye, Dan
Xu, Peng-Fei
Wei, Hao
Advanced Materials, 2020, 132 (32) : 23743 - 23749
[43] Carbon-hydrogen (C-H) bond activation at PdIV: A Frontier in C-H functionalization catalysis
Department of Chemistry, University of Michigan, Ann Arbor
MI
48108, United States
Chem. Sci., 2041, 1 (70-76):
[44] Pt-Catalyzed C-C Activation Induced by C-H Activation
Bowring, Miriam A.
Bergman, Robert G.
Tilley, T. Don
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (35) : 13121 - 13128
[45] Asymmetric Synthesis of α-Branched Amines via Rh(III)-Catalyzed C-H Bond Functionalization
Wangweerawong, Apiwat
Bergman, Robert G.
Ellman, Jonathan A.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (24) : 8520 - 8523
[46] Cobalt-Catalyzed Tandem C-H Activation/C-C Cleavage/C-H Cyclization of Aromatic Amides with Alkylidenecyclopropanes
Li, Mingliang
Kwong, Fuk Yee
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (22) : 6512 - 6516
[47] C-H Functionalization
Doyle, Michael P.
Goldberg, Karen I.
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) : 777 - 777
[48] The Role of Catalysts in Functionalization of C-H and C-C Bonds
Mostafa, Mohamed Mokhtar M.
Saleh, Tamer Said S.
Ahmed, Nerseen Said I.
CATALYSTS, 2023, 13 (02)
[49] 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
[50] C-H Functionalization
Davies, Huw M. L.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 1552 - 1553

← 1 2 3 4 5 →