Novel CuCl2-cryptand-[2.2.Benzo] complex: A base free and oxidant free catalyst for Ipso-Hydroxylation of aryl/heteroaryl-boronic acids in water at room temperature

被引：15

作者：

Bora, Sankar Jyoti ^{[1
]}

Chetia, Bolin ^{[1
]}

机构：

[1] Dibrugarh Univ, Dept Chem, Dibrugarh 786004, Assam, India

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2017年 / 851卷

关键词：

Cryptand; Phenols; Catalysis; Heterogeneous; Ipso-HydroxyLation; Water; ARYLBORONIC ACIDS; OXIDATIVE HYDROXYLATION; EFFICIENT CATALYST; PHENOLIC-COMPOUNDS; CROWN-ETHERS; LIGAND; COPPER; CRYPTAND-22; MILD; ARYL;

D O I：

10.1016/j.jorganchem.2017.09.011

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A novel cryptand and its copper complex was synthesised, which found to have enormous catalytic activity towards ipso-hydroxylation of aryl or heteroarylboronic acids and esters in water without using H2O2 or other oxidising agent and base at room temperature. This newly developed method efficiently converts aryl boronic acids and esters as well as heteroaryl boronic acids to their corresponding phenols with high yields within a very short reaction time. This protocol has found to be well-matched with a wide variety of functional groups. High yields, very short reaction time, easy separation, recyclability up to 6th time are the advantages of this method. (C) 2017 Elsevier B.V. All rights reserved.

引用

页码：52 / 56

页数：5

共 48 条

[1] Catalysis by mont K-10 supported silver nanoparticles: a rapid and green protocol for the efficient ipso-hydroxylation of arylboronic acids [J].

Begum, Tahshina ;

Gogoi, Ankur ;

Gogoi, Pradip K. ;

Bora, Utpal .

TETRAHEDRON LETTERS, 2015, 56 (01) :95-97

[2] On-water synthesis of phenols using biogenic Cu2O nanoparticles without using H2O2 [J].

Borah, Rupom ;

Saikia, Eramoni ;

Bora, Sankar Jyoti ;

Chetia, Bolin .

RSC ADVANCES, 2016, 6 (102) :100443-100447

[3] NMR Studies on Li+, Na+ and K+ Complexes of Orthoester Cryptand o-Me2-1.1.1 [J].

Brachvogel, Rene-Chris ;

Maid, Harald ;

von Delius, Max .

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2015, 16 (09) :20641-20656

[4] Organic hypervalent iodine(III) catalyzed ipso-hydroxylation of aryl- and alkylboronic acids/esters [J].

Chatterjee, Nachiketa ;

Goswami, Avijit .

TETRAHEDRON LETTERS, 2015, 56 (12) :1524-1527

[5] Synthesis and Crystal Structure Determination of [H2-cryptand 222](Br3)2: A Unique Tribromide Catalyst for the Catalytic Chemoselective N-Boc Protection of Amines [J].

Chehardoli, Gholamabbas ;

Zolfigol, Mohammad Ali ;

Khakyzadeh, Vahid ;

Golbedaghi, Reza ;

Hall, Nikita A. ;

Blackman, Allan G. .

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2011, 58 (04) :538-543

[6]

DIETRICH B, 1969, TETRAHEDRON LETT, P2885

[7] Aerobic oxidative C-B bond cleavage of arylboronic acids mediated by methylhydrazines [J].

Ding, Wei ;

Chen, Jia-Rong ;

Zou, You-Quan ;

Duan, Shu-Wen ;

Lu, Liang-Qiu ;

Xiao, Wen-Jing .

ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (02) :151-154

[8]

Directrich B., 1973, TETRAHEDRON, V29, P1629

[9] A mild and efficient protocol for the ipso-hydroxylation of arylboronic acids [J].

Gogoi, Ankur ;

Bora, Utpal .

TETRAHEDRON LETTERS, 2013, 54 (14) :1821-1823

[10] An Iodine-Promoted, Mild and Efficient Method for the Synthesis of Phenols from Arylboronic Acids [J].

Gogoi, Ankur ;

Bora, Utpal .

SYNLETT, 2012, (07) :1079-1081

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