Rhodium(III)-Catalyzed Regioselective C4 Alkylation of Indoles with Nitroalkenes

被引：0

作者：

Zhao, Ru ^{[1
]}

Lv, Xulin ^{[1
]}

Yang, Hao-Ran ^{[1
]}

Gao, Lijun ^{[1
]}

Zhou, Liming ^{[1
]}

Fang, Shaoming ^{[1
,2
]}

Liu, Shuang-Liang ^{[1
]}

机构：

[1] Zhengzhou Univ Light Ind, Coll Mat & Chem Engn, Zhengzhou 450001, Peoples R China

[2] Zhengzhou Univ Light Ind, Key Lab Surface & Interface Sci & Technol Henan Pr, Zhengzhou 450001, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 23期

基金：

中国国家自然科学基金;

关键词：

DIRECTING-GROUP; H ACTIVATION; FUNCTIONALIZATION; MALEIMIDES; ARYLATION;

D O I：

10.1021/acs.joc.4c02236

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Rh(III)-catalyzed indole C4-H bond addition to nitroalkenes is disclosed under mild and redox-neutral reaction conditions, offering straightforward access to various 4-(2-nitroalkyl)indoles (34 examples) with excellent chemo- and regioselectivity. Furthermore, late-stage diversifications and mechanistic studies were also performed.

引用

页码：17844 / 17849

页数：6

共 50 条

[41] Enantioselective Friedel-Crafts Alkylation between Nitroalkenes and Indoles Catalyzed by Charge Activated Thiourea Organocatalysts
Fan, Yang
Kass, Steven R.
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (24): : 13288 - 13296
[42] Cp*Co(III)-Catalyzed Regioselective C2 Amidation of Indoles Using Acyl Azides
Shah, Tariq A.
De, Pinaki Bhusan
Pradhan, Sourav
Banerjee, Sonbidya
Punniyamurthy, Tharmalingam
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (24): : 16278 - 16285
[43] Palladium-catalyzed regioselective C-H fluoroalkylation of indoles at the C4-position
Borah, Arun Jyoti
Shi, Zhuangzhi
CHEMICAL COMMUNICATIONS, 2017, 53 (28) : 3945 - 3948
[44] Co(III)-Catalyzed Regioselective C-H Dienylation of Indolines and Indoles with Allenyl Carbinol Acetates
Shukla, Rahul K.
Singh, Anurag
Shetty, Rakesh
Volla, Chandra M. R.
ADVANCED SYNTHESIS & CATALYSIS, 2025,
[45] Iron-catalyzed regioselective C-H alkylation of indoles: an additive-free approach in renewable solvent
Pradhan, Chandini
Jagtap, Rahul A.
Samal, Pragnya Paramita
Krishnamurty, Sailaja
Punji, Benudhar
GREEN CHEMISTRY, 2023, 25 (23) : 9733 - 9743
[46] Rh(III)-Catalyzed, Highly Selectively Direct C-H Alkylation of Indoles with Diazo Compounds
Wan, Kang
Li, Zhan
Qu, Xing
Wang, Feng
Wang, Liang
CATALYSTS, 2016, 6 (06):
[47] First Example of C-3 Alkylation of Indoles with Activated Azetidines Catalyzed by Indium(III) Bromide
Yadav, J. S.
Reddy, B. V. Subba
Narasimhulu, G.
Satheesh, G.
SYNLETT, 2009, (05) : 727 - 730
[48] Rhodium(III)-Catalyzed Arene and Alkene C-H Bond Functionalization Leading to Indoles and Pyrroles
Stuart, David R.
Alsabeh, Pamela
Kuhn, Michelle
Fagnou, Keith
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (51) : 18326 - 18339
[49] Rhodium(III)-Catalyzed Decarboxylative Aminomethylation of Glycine Derivatives with Indoles via C-H Activation
Liu, Ruixing
Wei, Yin
Shi, Min
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (04): : 2838 - 2845
[50] Rhodium(III)-catalyzed C-H allylation of indoles with allyl alcohols via β-hydroxide elimination
Wu, Xiaowei
Ji, Haitao
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (31) : 5691 - 5698

← 1 2 3 4 5 →