N-Heterocyclic carbene copper(I) complex-catalyzed synthesis of 2-aryl benzoxazoles and benzothiazoles

被引：43

作者：

Urzua, Julio I. ^{[1
]}

Contreras, Renato ^{[2
]}

Salas, Cristian O. ^{[1
]}

Tapia, Ricardo A. ^{[1
]}

机构：

[1] Pontificia Univ Catolica Chile, Fac Quim, Santiago 6094411, Chile

[2] Univ Chile, Fac Ciencias, Dept Quim, Casilla 653, Santiago, Chile

来源：

RSC ADVANCES | 2016年 / 6卷 / 85期

关键词：

INTRAMOLECULAR O-ARYLATION; ONE-POT SYNTHESIS; C-H BOND; CROSS-COUPLING REACTIONS; 2-SUBSTITUTED BENZOTHIAZOLES; CARBONYL-COMPOUNDS; DECARBOXYLATIVE ARYLATION; SUBSTITUTED BENZOXAZOLES; PALLADIUM COMPLEXES; ARYL CHLORIDES;

D O I：

10.1039/c6ra18510j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new and efficient synthesis of 2-arylbenzoxazoles and benzothiazoles using a copper N-heterocyclic carbene complex is described. In a simple protocol a variety of 2-substituted benzoxazoles and benzothiazoles were obtained via intramolecular coupling cyclization of 2-haloanilides/2-halothioanilides in good to excellent yields.

引用

页码：82401 / 82408

页数：8

共 50 条

[21] N-Heterocyclic Carbene Catalyzed [2+2] Cycloaddition of Aryl Isothiocyanates and Nitroolefins: An Efficient Synthesis of β-Thiolactams
Awasthi, Chhama
Yadav, Lal Dhar S.
SYNLETT, 2010, (12) : 1783 - 1788
[22] Markovnikov-Selective Hydroboration of Olefins Catalyzed by a Copper N-Heterocyclic Carbene Complex
DiBenedetto, Tarah A.
Parsons, Astrid M.
Jones, William D.
ORGANOMETALLICS, 2019, 38 (17) : 3322 - 3326
[23] N-Heterocyclic Carbene (NHC)/Ag(I) Co-catalyzed Synthesis of 2-Oxo-2-arylethyl Aryl Formates
Cheng, Li
Wang, Wenrong
Sun, Yuqian
Li, Tuanjie
Yu, Chenxia
Yao, Changsheng
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (04) : 1607 - 1613
[24] Cyclopropenation of internal alkynylsilanes and diazoacetates catalyzed by copper(I) N-heterocyclic carbene complexes
Thomas, Thomas J.
Merritt, Benjamin A.
Lemma, Betsegaw E.
Mckoy, Adina M.
Tri Nguyen
Swenson, Andrew K.
Mills, Jeffrey L.
Coleman, Michael G.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (05) : 1742 - 1747
[25] Benchtop synthesis and crystal structure determination of a monomeric N-heterocyclic carbene complex of copper(I) chloride
McLean, Anna P.
Neuhardt, Elizabeth A.
St John, Joel P.
Findlater, Michael
Abernethy, Colin D.
TRANSITION METAL CHEMISTRY, 2010, 35 (04) : 415 - 418
[26] Synthesis and Applications of Copper N-heterocyclic Carbene Complexes
Liu Bo
Chen Wan-Zhi
CHINESE JOURNAL OF INORGANIC CHEMISTRY, 2014, 30 (01) : 20 - 36
[27] Benchtop synthesis and crystal structure determination of a monomeric N-heterocyclic carbene complex of copper(I) chloride
Anna P. McLean
Elizabeth A. Neuhardt
Joel P. St. John
Michael Findlater
Colin D. Abernethy
Transition Metal Chemistry, 2010, 35 : 415 - 418
[28] N-Heterocyclic Carbene Complexes of Copper(I) Thiocyanate: Synthesis and Structural Characterization
Dodds, Christopher A.
Kennedy, Alan R.
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2014, 640 (05): : 926 - 930
[29] Synthesis and Structural Study of a N-Heterocyclic Carbene Trinuclear Silver(I) Complex
Liu Jun
Huo Ran
Wei Qing
Zhao Zhi-Xiang
Liu Qing-Xiang
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2016, 35 (02) : 313 - 318
[30] Synthesis of N-heterocyclic carbene gold(I) complexes
Fady Nahra
Nikolaos V. Tzouras
Alba Collado
Steven P. Nolan
Nature Protocols, 2021, 16 : 1476 - 1493

← 1 2 3 4 5 →