Palladium-catalyzed direct C-H allylation of indoles derivatives with allyltrimethylsilanes

被引：0

作者：

Wang, Lun ^{[1
]}

He, Yuanhao ^{[2
]}

Li, Zhi ^{[1
]}

Zhang, Linchun ^{[2
]}

Fan, Baoming ^{[1
,2
]}

Zhao, Fen ^{[1
]}

Chen, Minghong ^{[1
]}

机构：

[1] Yunnan Minzu Univ, Sch Chem & Environm, Kunming 650504, Yunnan, Peoples R China

[2] Yunnan Minzu Univ, Key Lab Chem Ethn Med Resource, Kunming 650504, Yunnan, Peoples R China

来源：

TETRAHEDRON LETTERS | 2023年 / 129卷

基金：

中国国家自然科学基金;

关键词：

Palladium; -catalyzed; C-H activation; Allylation; Allyltrimethylsilanes; Indoles; ORTHO-ARYLATION; CARBONYL-COMPOUNDS; ALLYLIC ALCOHOLS; BONDS; FUNCTIONALIZATION; ACTIVATION; SILICON; ARYLSILANES; ALKYLATION; REAGENTS;

D O I：

10.1016/j.tetlet.2023.154689

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed cross-coupling reaction between 2-susbtituted indole and allyltrimethylsilanes in the absence of fluoride anion source was studied. The optimal conditions for the reaction were identified after various reaction conditions examined, using Pd(OAc)2 as the catalyst, Cu(OTf)2 as oxidant, and DMSO as solvent, leading to the synthesis of a series of benzindoles bearing allyl group in good to high yields.

引用

页数：4

共 50 条

[1] Regioselective Palladium-Catalyzed C-H Bond Trifluoroethylation of Indoles: Exploration and Mechanistic Insight
Zhang, Hao
Wang, Hao-Yang
Luo, Yixin
Chen, Chaohuang
Cao, Yimiao
Chen, Pinhong
Guo, Yin-Long
Lan, Yu
Liu, Guosheng
ACS CATALYSIS, 2018, 8 (03): : 2173 - 2180
[2] Palladium-Catalyzed Direct C-H Alkylation of Electron-Deficient Pyrrole Derivatives
Jiao, Lei
Bach, Thorsten
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (23) : 6080 - 6083
[3] Direct carboxamidation of indoles by palladium-catalyzed C-H activation and isocyanide insertion
Peng, Jiangling
Liu, Lanying
Hu, Ziwei
Huang, Jinbo
Zhu, Qiang
CHEMICAL COMMUNICATIONS, 2012, 48 (31) : 3772 - 3774
[4] Palladium-Catalyzed Direct C-H Arylation of Dicyanobenzenes
Ihanainen, Netta E.
Kumpulainen, Esa T. T.
Koskinen, Ari M. P.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (15) : 3226 - 3229
[5] Palladium-Catalyzed Direct Monoarylation of Aryl C-H Bonds with Iodoarenes
Su, Li
Guo, Dong-Dong
Li, Bin
Guo, Shi-Huan
Pan, Gao-Fei
Gao, Ya-Ru
Wang, Yong-Qiang
CHEMCATCHEM, 2017, 9 (11) : 2001 - 2008
[6] Palladium-Catalyzed Oxidative C-H/C-H Cross-Coupling of Indoles and Pyrroles with Heteroarenes
Wang, Zhen
Li, Kaizhi
Zhao, Dongbing
Lan, Jingbo
You, Jingsong
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (23) : 5365 - 5369
[7] Palladium-catalyzed oxidative direct C-H/C-H cross coupling of anilides with β-keto esters
Chan, Wai-Wing
Zhou, Zhongyuan
Yu, Wing-Yiu
CHEMICAL COMMUNICATIONS, 2013, 49 (74) : 8214 - 8216
[8] Palladium-Catalyzed C-H Acetoxylation Reations
Chen, Tianbao
Zhang, Ming
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (04) : 813 - 826
[9] Palladium-catalyzed regioselective C-H fluoroalkylation of indoles at the C4-position
Borah, Arun Jyoti
Shi, Zhuangzhi
CHEMICAL COMMUNICATIONS, 2017, 53 (28) : 3945 - 3948
[10] Palladium-Catalyzed Direct Alkynylation of C-H Bonds in Benzenes
Tobisu, Mamoru
Ano, Yusuke
Chatani, Naoto
ORGANIC LETTERS, 2009, 11 (15) : 3250 - 3252

← 1 2 3 4 5 →