(Pentamethylcyclopentadienyl)cobalt(III)-Catalyzed Oxidative [4+2] Annulation of N-H Imines with Alkynes: Straightforward Synthesis of Multisubstituted Isoquinolines

被引：59

作者：

Zhang, Shang-Shi ^{[1
]}

Liu, Xu-Ge ^{[1
]}

Chen, Shi-Yong ^{[1
]}

Tan, Dong-Hang ^{[1
]}

Jiang, Chun-Yong ^{[1
]}

Wu, Jia-Qiang ^{[1
]}

Li, Qingjiang ^{[1
]}

Wang, Honggen ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 10期

基金：

中国国家自然科学基金;

关键词：

annulation; cerium salts; C-H activation; cobalt; isoquinolines; CARBON-CARBON BONDS; C-H; INTERNAL ALKYNES; COBALT(III)-CATALYZED ARYL; DIRECT FUNCTIONALIZATION; BETA-PHENYLETHYLAMINES; ASYMMETRIC CATALYSIS; IRIDIUM COMPLEXES; MILD CONDITIONS; ACTIVATION;

D O I：

10.1002/adsc.201600025

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A synthetic method for isoquinoline synthesis via a [4+2] annulation of N-H imines with alkynes using the high-valent (pentamethylcyclopentadienyl)cobalt(III) [Cp*Co(III)] catalyst is described. Cerium(IV) sulfate was found to be an efficient oxidant in lieu of the commonly used copper or silver salts. Broad substrate scope, high functional group tolerance, and generally good yields were observed.

引用

页码：1705 / 1710

页数：6

共 50 条

[41] Rhodium(III)-Catalyzed [4+2] Annulation of N-Hydroxyoximes with Maleate Esters/2-Chloroacrylates: Synthesis of Isoquinoline-3,4-Dicarboxylates and Isoquinoline-3-Carboxylates
Li, He
Chen, Tao
Wang, Zhiwei
Li, Yuxin
Wu, Baoheng
Xu, Ning
Lu, Ye
Jin, Xinxin
Yu, Jiaqi
Liu, Jinglin
Bao, Ming
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 28 (08)
[42] Salicylaldehyde-Promoted Cobalt-Catalyzed C-H/N-H Annulation of Indolyl Amides with Alkynes: Direct Synthesis of a 5-HT3 Receptor Antagonist Analogue
Huang, Mao-Gui
Shi, Shuai
Li, Ming
Liu, Yue-Jin
Zeng, Ming-Hua
ORGANIC LETTERS, 2021, 23 (18) : 7094 - 7099
[43] N-Heterocyclic Carbene Catalyzed Generation and [4+2] Annulation of Unsubstituted Dienolate - Enantioselective Synthesis of Spirocyclic Oxindolodihydropyranones
Cheng, Jin-Tang
Chen, Xiang-Yu
Gao, Zhong-Hua
Ye, Song
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (05) : 1047 - 1053
[44] Rhodium(III)-Catalyzed Oxidative Annulation of 2,2′-Bipyridine N-Oxides with Alkynes via Dual C-H Bond Activation
Xu, Xin
Zhao, Haoqiang
Xu, Jianbin
Chen, Changjun
Pan, Yixiao
Luo, Zhenli
Zhang, Zongyao
Li, Huanrong
Xu, Lijin
ORGANIC LETTERS, 2018, 20 (13) : 3843 - 3847
[45] Synthesis of 3-Methyleneisoindolin-1-ones via Rhodium(III)-Catalyzed C-H/N-H Activation and Annulation of N-Methoxybenzamides with Potassium Vinyltrifluoroborate
Kumar, Vikash
Gandeepan, Parthasarathy
CHEMISTRY-AN ASIAN JOURNAL, 2024, 19 (22)
[46] Rhodium(III)-catalyzed synthesis of indoles from 1-alkylidene-2-arylhydrazines and alkynes via C-H and N-N bond cleavages
Matsuda, Takanori
Tomaru, Yuki
TETRAHEDRON LETTERS, 2014, 55 (22) : 3302 - 3304
[47] Computational Mechanistic Study on the Nickel-Catalyzed C-H/N-H Oxidative Annulation of Aromatic Amides with Alkynes: The Role of the Nickel (0) Ate Complex
Yamazaki, Ken
Obata, Atsushi
Sasagawa, Akane
Ano, Yusuke
Chatani, Naoto
ORGANOMETALLICS, 2019, 38 (02) : 248 - 255
[48] Rhodium-catalyzed oxidative annulation of 1H-indazoles with alkynes for the synthesis of indazolo[3,2-a]isoquinolines via C-H bond functionalization
Huang, Jian
Fu, Yang
Deng, Zhihong
Chen, Wei
Song, Zhibin
Peng, Yiyuan
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (48) : 9863 - 9872
[49] Synthesis of 9,10-Phenanthrenes via Rh(III)-Catalyzed [4+2] Annulation of 2-Biphenylboronic Acids with Diazo Compounds
Tian, Miaomiao
Yang, Lingyun
Liu, Bingxian
Chang, Junbiao
CHINESE JOURNAL OF CHEMISTRY, 2023, 41 (11): : 1327 - 1332
[50] Reverse Regioselective Cp*Co(III)-Catalyzed [4+2] C-H Annulation of N-Chloroamides with Vinylsilanes: Synthesis of 4-Silylated Isoquinolones and Their Synthetic Utilities
Ghosh, Arijit
Rana, Tamanna
Bhaduri, Nilanjan
Pawar, Amit B.
ORGANIC LETTERS, 2023, 25 (43) : 7878 - 7883

← 1 2 3 4 5 →