Synthesis of Benzoxazole and Benzimidazole Derivatives via Ligand-Free Copper(I)-Catalyzed Cross-Coupling Reaction of o-Halophenols or o-Haloanilines with Carbodiimides

被引：57

作者：

Shen, Guodong ^{[1
]}

Bao, Weiliang ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Zhejiang, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 06期

关键词：

copper(I) catalysis; cross-coupling; heterocycles; ligand-free conditions; one-pot reaction; STREPTOMYCES SP 517-02; STRUCTURE-BASED DESIGN; N BOND FORMATION; C-N; EFFICIENT SYNTHESIS; CYTOTOXIC METABOLITE; CATALYZED SYNTHESIS; COPPER; ARYLATION; NITROGEN;

D O I：

10.1002/adsc.201000022

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A novel and efficient synthesis of benzoxazole and benzimidazole derivatives via a ligand-free, copper(I)-catalyzed, one-pot cascade process has been developed. A variety of carbodiimides coupled with o-halophenols or o-haloanilines to give the products in moderate to excellent yields under the mild conditions.

引用

页码：981 / 986

页数：6

共 50 条

[41] Facile synthesis of 2-bromoindoles by ligand-free CuI-catalyzed intramolecular cross-coupling of gem-dibromoolefins
Jiang, Baishan
Tao, Kemei
Shen, Wang
Zhang, Jiancun
TETRAHEDRON LETTERS, 2010, 51 (48) : 6342 - 6344
[42] Maghemite-Copper Nanocomposites: Applications for Ligand-Free Cross-Coupling (C-O, C-S, and C-N) Reactions
Sharma, Rakesh K.
Gaur, Rashmi
Yadav, Manavi
Rathi, Anuj K.
Pechousek, Jiri
Petr, Martin
Zboril, Radek
Gawande, Manoj B.
CHEMCATCHEM, 2015, 7 (21) : 3495 - 3502
[43] Indole Synthesis by Conjugate Addition of Anilines to Activated Acetylenes and an Unusual Ligand-Free Copper(II)-Mediated Intramolecular Cross-Coupling
Gao, Detian
Back, Thomas G.
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (46) : 14828 - 14840
[44] Accessing Heteroannular Benzoxazole and Benzimidazole Scaffolds via Carbodiimides Using Azide-Isocyanide Cross-Coupling as Catalyzed by Mesoionic Singlet Palladium Carbene Complexes Derived from a Phenothiazine Moiety
Dey, Shreyata
Ghosh, Prasenjit
ACS OMEGA, 2023, 8 (12): : 11039 - 11064
[45] C-N cross-coupling reaction catalysed by reusable CuCr2O4 nanoparticles under ligand-free conditions: a highly efficient synthesis of triarylamines
Safaei-Ghomi, Javad
Akbarzadeh, Zeinab
Khojastehbakht-Koopaei, Bahareh
RSC ADVANCES, 2015, 5 (37): : 28879 - 28884
[46] Bio-surfactant: a green and environmentally benign reaction medium for ligand-free Pd-catalyzed Mizoroki–Heck cross-coupling reaction in water
Seema P. Patil
Sanjay N. Jadhav
Chandrashekhar V. Rode
Rajendra V. Shejwal
Arjun S. Kumbhar
Transition Metal Chemistry, 2020, 45 : 403 - 411
[47] Synthesis of benzoxazoles via an iron-catalyzed domino C-N/C-O cross-coupling reaction
Yang, Bo
Hu, Weiye
Zhang, Songlin
RSC ADVANCES, 2018, 8 (05): : 2267 - 2270
[48] Synthesis of Biaryls via Ligand-Free Suzuki-Miyaura Cross-Coupling Reactions: A Review of Homogeneous and Heterogeneous Catalytic Developments
Hussain, Ibrar
Capricho, Jaworski
Yawer, Mirza A.
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (21) : 3320 - 3349
[49] Water-Soluble Copper(I) Hydroxide Catalyst and Its Formation in Ligand-Free Suzuki-Miyaura Cross-Coupling Reactions
Karna, Priya
Finfrock, Zou
Li, Junjie
Hu, Yongfeng
Yang, Dong-Sheng
JOURNAL OF PHYSICAL CHEMISTRY C, 2023, 127 (12): : 5791 - 5799
[50] Improved and ligand-free copper-catalyzed cyclization for an efficient synthesis of benzimidazoles from o-bromoarylamine and nitriles
Bonku, Emmanuel Mintah
Qin, Hongjian
Odilov, Abdullajon
Abduahadi, Safomuddin
Guma, Samuel Desta
Yang, Feipu
Zhu, Fuqiang
Aisa, Haji A.
Shen, Jingshan
RSC ADVANCES, 2024, 14 (10) : 6906 - 6916

← 1 2 3 4 5 →