TBAF-Assisted Copper-Catalyzed N-Arylation and Benzylation of Benzazoles with Aryl and Benzyl Halides under the Ligand/Base/Solvent-Free Conditions

被引：46

作者：

Lee, Hyung-Geun ^{[1
]}

Won, Ju-Eun ^{[1
]}

Kim, Min-Jung ^{[1
]}

Park, Song-Eun ^{[1
]}

Jung, Kwang-Ju ^{[1
]}

Kim, Bo Ram ^{[1
]}

Lee, Sang-Gyeong ^{[1
]}

Yoon, Yong-Jin ^{[1
]}

机构：

[1] Gyeongsang Natl Univ, Dept Chem & Environm Biotechnol, Natl Core Res Ctr, Res Inst Nat Sci,Grad Sch Mol Mat & Nanochem, Jinju 660701, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 15期

关键词：

PHASE-TRANSFER CATALYSIS; HETEROARYL HALIDES; ULLMANN SYNTHESIS; EFFICIENT; IMIDAZOLES; INHIBITORS; BENZOTRIAZOLE; HETEROCYCLES; RECEPTOR; SOLVENT;

D O I：

10.1021/jo900752z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

TBAF-assisted N-arylation and benzylation of benzazoles such as I H-benzimidazole, 1H-indole, and 1H-benzotriazole with aryl and benzyl halides have been demonstrated tinder the ligand/base/solvent-free conditions. In the presence of CuBr2 and TBAF (n-Bu4NF), the azoles underwent N-arylation and benzylation with aryl and benzyl halides smoothly in moderate to good yields. It is noteworthy that the reaction is conducted under the ligand/base/solvent-free conditions.

引用

页码：5675 / 5678

页数：4

共 50 条

[1] Solvent-free copper-catalyzed N-arylation of amino alcohols and diamines with aryl halides
Yin, Huiqing
Jin, Ming
Chen, Wei
Chen, Chen
Zheng, Likang
Wei, Ping
Han, Shiqing
[J]. TETRAHEDRON LETTERS, 2012, 53 (10) : 1265 - 1270
[2] Practical copper-catalyzed N-arylation of nitrogen heterocycles with aryl halides under ligand and additive free conditions
Chang, Joyce Wei Wei
Xu, Xiuhui
Chan, Philip Wai Hong
[J]. TETRAHEDRON LETTERS, 2007, 48 (02) : 245 - 248
[3] Microwave Assisted, Solvent- and Ligand-Free Copper Catalyzed N-Arylation of Phenylurea with Aryl Halides
Gavade, Sandip
Shingare, Murlidhar
Mane, Dhananjay
[J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (12) : 4167 - 4170
[4] Efficient ligand-free copper-catalyzed N-arylation of amides with aryl halides in water
Yong, Fui-Fong
Teo, Yong-Chua
Chua, Guan-Leong
Lim, Gina Shiyun
Lin, Yizhen
[J]. TETRAHEDRON LETTERS, 2011, 52 (11) : 1169 - 1172
[5] Mild copper-catalyzed N-arylation of azaheterocycles with aryl halides
Kuil, M
Bekedam, EK
Visser, GM
van den Hoogenband, A
Terpstra, JW
Kamer, PCJ
van Leeuwen, PWNM
van Strijdonck, GPF
[J]. TETRAHEDRON LETTERS, 2005, 46 (14) : 2405 - 2409
[6] Ligand free copper-catalyzed N-arylation of heteroarylamines
Wang, Deping
Kuang, Daizhi
Zhang, Fuxing
Liu, Yang
Ning, Shunhua
[J]. TETRAHEDRON LETTERS, 2014, 55 (51) : 7121 - 7123
[7] Copper-catalyzed N-arylation of 2-arylindoles with aryl halides
Liu, Wei
Han, Li-Ya
Liu, Rui-Li
Xu, Li-Ge
Bi, Yan-Lan
[J]. CHINESE CHEMICAL LETTERS, 2014, 25 (09) : 1240 - 1243
[8] Copper-catalyzed N-arylation of 2-arylindoles with aryl halides
Wei Liu
Li-Ya Han
Rui-Li Liu
Li-Ge Xu
Yan-Lan Bi
[J]. Chinese Chemical Letters, 2014, 25 (09) : 1240 - 1243
[9] Copper catalyzed N-arylation of sulfonamides with aryl bromides under ligand-free conditions
Teo, Yong-Chua
Tan, Yun-Ru
Saanvi, M. Kyra
Loh, Chu-Ken
Tan, Swee-Ngin
[J]. SYNTHETIC COMMUNICATIONS, 2023, 53 (14) : 1143 - 1152
[10] Commercial drug norfloxacin as a novel ligand for the copper-catalyzed N-arylation of imidazole with aryl halides
Wu, Fengtian
Nan, Chenlong
Ma, Minyang
Li, Huiqin
Xie, Jianwei
[J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (11)

← 1 2 3 4 5 →