Substrate-promoted copper-catalyzed N-arylation of amino alcohols with aryl iodides in water

被引：8

作者：

Jin, Ming ^{[1
]}

Zhao, Dan ^{[1
]}

He, Guozhen ^{[1
]}

Tong, Yao ^{[1
]}

Han, Shiqing ^{[1
]}

机构：

[1] Nanjing Univ Technol, Coll Biotechnol & Pharmaceut Engn, Nanjing 211816, Jiangsu, Peoples R China

来源：

CHINESE JOURNAL OF CATALYSIS | 2013年 / 34卷 / 09期

基金：

中国国家自然科学基金; 国家高技术研究发展计划(863计划);

关键词：

Amino alcohol; Aqueous phase; Copper catalyst; N-Arylation reaction; Substrate promotion; NITROGEN-CONTAINING HETEROCYCLES; BOND-FORMING REACTIONS; O-ARYLATION; EFFICIENT; HALIDES; LIGAND; MILD; AMINATION; BROMIDES; AMIDATION;

D O I：

10.1016/S1872-2067(12)60623-8

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient method has been developed for the N-arylation of a variety of water-soluble amino alcohols (1.2 mmol) with aryl iodides (1.0 mmol) in water under CuI-catalyzed conditions. The reaction was conducted via substrate-promoted action and did not require an additional ligand or phase-transfer catalyst, and afforded the desired N-aryl amines in acceptable to excellent yields (64%-93%) under mild reaction conditions with a small excess of the amino alcohol. (C) 2013, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.

引用

页码：1651 / 1655

页数：5

共 50 条

[21] Copper-catalyzed N-arylation of imidazoles and benzimidazoles
Altman, Ryan A.
Koval, Erica D.
Buchwald, Stephen L.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16): : 6190 - 6199
[22] Copper-catalyzed coupling of aryl iodides with aliphatic alcohols
Wolter, M
Nordmann, G
Job, GE
Buchwald, SL
[J]. ORGANIC LETTERS, 2002, 4 (06) : 973 - 976
[23] Ligand-free copper nanoparticle promoted N-arylation of azoles with aryl and heteroaryl iodides
Pai, Gita
Chattopadhyay, Asoke P.
[J]. TETRAHEDRON LETTERS, 2014, 55 (04) : 941 - 944
[24] Copper-catalyzed N-arylation of sulfonamides with aryl bromides under mild conditions
Wang, Xiang
Guram, Anil
Ronk, Michael
Milne, Jacqueline E.
Tedrow, Jason S.
Faul, Margaret M.
[J]. TETRAHEDRON LETTERS, 2012, 53 (01) : 7 - 10
[25] Copper-Catalyzed α-Arylation of Nitroalkanes with (Hetero)aryl Bromides/Iodides
Huang, Jianqiang
Li, Taian
Lu, Xiaobiao
Ma, Dawei
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (07)
[26] Microwave-enhanced copper-catalyzed n-arylation of free and protected amino acids in water
Rottger, Svenja
Sjoberg, Per J. R.
Larhed, Mats
[J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2007, 9 (02): : 204 - 209
[27] Palladium-catalyzed N-arylation of sulfoximines with aryl bromides and aryl iodides
Bolm, C
Hildebrand, JP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (01): : 169 - 175
[28] Copper-Catalyzed N-Arylation of Indoles and Anilines with Aryltrialkoxysilanes
Xie, Qi
Zhang, Xiuqi
Liu, Huijin
Zhang, Fukuan
Luo, Xuzhong
Luo, Haiqing
[J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (03)
[29] Mild Conditions for Copper-Catalyzed N-Arylation of Imidazoles
Chen, Huaming
Wang, Deping
Wang, Xianyang
Huang, Wenlong
Cai, Qian
Ding, Ke
[J]. SYNTHESIS-STUTTGART, 2010, (09): : 1505 - 1511
[30] Copper-catalyzed sequential N-arylation of C-amino-NH-azoles
Rao, D. Nageswar
Rasheed, Sk.
Vishwakarma, Ram A.
Das, Parthasarathi
[J]. CHEMICAL COMMUNICATIONS, 2014, 50 (85) : 12911 - 12914

← 1 2 3 4 5 →