A Highly Versatile Catalytic System for N-Arylation of Amines with Aryl Chlorides in Water

被引：27

作者：

Huang, Manna ^{[1
]}

Lin, Xiaoqin ^{[1
]}

Zhu, Xinhai ^{[1
]}

Peng, Weili ^{[1
]}

Xie, Jianwei ^{[1
]}

Wan, Yiqian ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Sch Chem & Chem Engn, Guangzhou 510275, Guangdong, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 24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：

Copper; Cross-coupling; Amination; Water chemistry; EFFICIENT COPPER CATALYST; HETEROATOM BOND FORMATION; CROSS-COUPLING REACTIONS; C-N; HALIDES; AMINATION; ULLMANN; PALLADIUM; LIGANDS; IODIDES;

D O I：

10.1002/ejoc.201100458

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The C-N coupling between nucleophiles and aryl chlorides, which are less expensive, less reactive, and more abundant than their bromide and iodide counterparts, is challenging but of great interest for industrial applications. An oxalyldihydrazide/hexane-2,5-dione (100-150 mol-%)/CuO system was found to enable the reaction of a wide range of nucleophiles with a variety of aryl chlorides in water for the first time.

引用

页码：4523 / 4527

页数：5

共 50 条

[31] Effect of Aryl Ligand Identity on Catalytic Performance of Trineopentylphosphine Arylpalladium Complexes in N-Arylation Reactions
Hu, Huaiyuan
Burlas, Corrie E.
Curley, Sabrina J.
Gruchala, Tomasz
Qu, Fengrui
Shaughnessy, Kevin H.
[J]. ORGANOMETALLICS, 2020, 39 (20) : 3618 - 3627
[32] A General Palladium-Phosphine Complex To Explore Aryl Tosylates in the N-Arylation of Amines: Scope and Limitations
Choy, Pui Ying
Chung, Kin Ho
Yang, Qingjing
So, Chau Ming
Sun, Raymond Wai-Yin
Kwong, Fuk Yee
[J]. CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (17) : 2465 - 2474
[33] Copper Catalyzed N-Arylation of Amines in Ionic Liquid Using 1-Aryltriazenes as Aryl Surrogates
Kim, Kang M.
Kim, Kang Min
[J]. CHEMISTRYSELECT, 2021, 6 (11): : 2709 - 2715
[34] Efficient N-Arylation/Dealkylation of Electron Deficient Heteroaryl Chlorides and Bicyclic Tertiary Amines under Microwave Irradiation
Wang, Hong-Jun
Wang, Yi
Csakai, Adam J.
Earley, William G.
Herr, R. Jason
[J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2009, 11 (03): : 355 - 363
[35] On water N-arylation of oxetanylamines for the preparation of N-aryl-oxetanylamines; potentially useful aryl-amide isosteres
Bollenbach, Maud
Lecroq, William
Wagner, Patrick
Fessard, Thomas
Schmitt, Martine
Salome, Christophe
[J]. CHEMICAL COMMUNICATIONS, 2019, 55 (11) : 1623 - 1626
[36] Versatile palladium-catalyzed arylation of organomanganese chlorides by aryl bromides
Riguet, E
Alami, M
Cahiez, G
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) : 376 - 379
[37] Palladium-Catalyzed N-Arylation of Amines and Amides with Aryltrimethylgermanes
Zhang, Qiang
Liu, Cunfang
Shi, Juan
Xu, Qiong
Jin, Lingxia
Zhao, Chaibin
Zhang, Tianlei
[J]. SYNLETT, 2016, 27 (13) : 1945 - 1948
[38] METALLIC COPPER CATALYSIS OF N-ARYLATION OF AMINES BY TRIARYLBISMUTH DIACYLATES
BARTON, DHR
FINET, JP
KHAMSI, J
[J]. TETRAHEDRON LETTERS, 1986, 27 (31) : 3615 - 3618
[39] Aryl Bromides and Aryl Chlorides for the Direct Arylation of Benzylic Amines Mediated by Ruthenium(II)
Dastbaravardeh, Navid
Schnuerch, Michael
Mihovilovic, Marko D.
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (14) : 2878 - 2890
[40] Chan–Lam N-Arylation of Adamantane-Containing Amines
D. S. Kuliukhina
A. S. Malysheva
A. D. Averin
E. N. Savelyev
B. S. Orlinson
I. A. Novakov
I. P. Beletskaya
[J]. Russian Journal of Organic Chemistry, 2023, 59 : 2107 - 2116

← 1 2 3 4 5 →