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

被引：16

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] A Direct Palladium-Catalyzed Route for the Synthesis of Benzo[a]carbazoles through Sequential C-C Bond Formation and C-H Bond Functionalization
Kianmehr, Ebrahim
Ghanbari, Mohammad
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (02) : 256 - 259
[42] Ruthenium-Catalyzed Regioselective C2 Alkenylation of Indoles and Pyrroles via C-H Bond Functionalization
Li, Bin
Ma, Jianfeng
Xie, Weijia
Song, Haibin
Xu, Shansheng
Wang, Baiquan
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (18) : 9345 - 9353
[43] Rhodium-Catalyzed C-H Amination: A Case Study of Selectivity in C-H Functionalization Reactions
Mack, James B. C.
Bedell, T. Aaron
DeLuca, Ryan J.
Hone, Graham A. B.
Roizen, Jennifer L.
Cox, Charles T.
Sorensen, Erik J.
Du Bois, J.
JOURNAL OF CHEMICAL EDUCATION, 2018, 95 (12) : 2243 - 2248
[44] Exploiting Strained Rings in Chelation Guided C-H Functionalization: Integration of C-H Activation with Ring Cleavage
Shah, Tariq A.
De, Pinaki Bhusan
Pradhan, Sourav
Banerjee, Sonbidya
Punniyamurthy, Tharmalingam
CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (24) : 4520 - 4533
[45] Divergent Functionalization of Indoles with Acryloyl Silanes via Rhodium-Catalyzed C-H Activation
Lu, Ping
Feng, Chao
Loh, Teck-Peng
ORGANIC LETTERS, 2015, 17 (13) : 3210 - 3213
[46] Rh(III)-Catalyzed Oxidative Coupling of Unactivated Alkenes via C-H Activation
Tsai, Andy S.
Brasse, Mikael
Bergman, Robert G.
Ellman, Jonathan A.
ORGANIC LETTERS, 2011, 13 (03) : 540 - 542
[47] Catalytic C-H Bond Functionalization of Cyclopropane Derivatives
Roman, Daniela Sustac
Charette, Andre B.
C-H BOND ACTIVATION AND CATALYTIC FUNCTIONALIZATION II, 2016, 56 : 91 - 113
[48] Iridium-Catalyzed Hydroarylation via C-H Bond Activation
Nishimura, Takahiro
CHEMICAL RECORD, 2021, 21 (12) : 3532 - 3545
[49] Oxygen as an oxidant in rhodium(III) catalyzed oxidative C-H/C-H cross-coupling between indoles and oxazoles
Wang, Yan
Lan, Jingbo
SCIENCE CHINA-CHEMISTRY, 2018, 61 (02) : 200 - 205
[50] Palladium(II)-Catalyzed Oxidative C-H/C-H Coupling and Eliminative SNH Reactions in Direct Functionalization of Imidazole Oxides with Indoles
Varaksin, Mikhail V.
Utepova, Irina A.
Chupakhin, Oleg N.
Charushin, Valery N.
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (20) : 9087 - 9093

← 1 2 3 4 5 →