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

[31] Methane challenge: C-H bond activation and C-C coupling
Schwarz, Helmut
Geng, Caiyun
Li, Jilai
Sun, Xiaoyan
Yue, Lei
Zhou, Shaodong
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
[32] Nickel-Catalyzed C-H Bond Functionalization of Azoles and Indoles
Jagtap, Rahul A.
Punji, Benudhar
CHEMICAL RECORD, 2021, 21 (12): : 3573 - 3588
[33] Application of C-H and C-C bond activation in organic synthesis
Jun, CH
Lee, JH
PURE AND APPLIED CHEMISTRY, 2004, 76 (03) : 577 - 587
[34] Ruthenium(II)-Catalyzed C-H Bond Activation and Functionalization
Arockiam, Percia Beatrice
Bruneau, Christian
Dixneuf, Pierre H.
CHEMICAL REVIEWS, 2012, 112 (11) : 5879 - 5918
[35] Transition-Metal-Catalyzed C-C Bond Macrocyclization via Intramolecular C-H Bond Activation
Wang, Xiao
Lu, Ming-Zhu
Loh, Teck-Peng
CATALYSTS, 2023, 13 (02)
[36] Rh(iii)-catalyzed C-H/C-C bond annulation of enaminones with iodonium ylides to form isocoumarins
Yang, Zi
Liu, Chaoshui
Lei, Jieni
Zhou, Yi
Gao, Xiaohui
Li, Yaqian
CHEMICAL COMMUNICATIONS, 2022, 58 (97) : 13483 - 13486
[37] Rh(III)-Catalyzed [3+2] Annulation and C-H Alkenylation of Indoles with 1,3-Diynes by C-H Activation
Kumar, Sanjeev
Nunewar, Saiprasad
Usama, Khan Mohammad
Kanchupalli, Vinaykumar
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (15) : 2223 - 2229
[38] Isocanthine Synthesis via Rh(III)-Catalyzed Intramolecular C-H Functionalization
Chen, Anthony Y.
Lu, Qianqian
Fu, Yao
Sarpong, Richmond
Stoltz, Brian M.
Zhang, Haiming
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (01): : 330 - 337
[39] Carbon-hydrogen (C-H) bond activation at PdIV: a Frontier in C-H functionalization catalysis
Topczewski, Joseph J.
Sanford, Melanie S.
CHEMICAL SCIENCE, 2015, 6 (01) : 70 - 76
[40] 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
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (52) : 23537 - 23543

← 1 2 3 4 5 →