Simple preparation of polymer supported IBX esters and amides and their oxidative properties

被引：69

作者：

Chung, WJ ^{[1
]}

Kim, DK ^{[1
]}

Lee, YS ^{[1
]}

机构：

[1] Seoul Natl Univ, Sch Chem Engn, Kwanak Ku, Seoul 151744, South Korea

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 52期

关键词：

polymer supported IBX ester; polymer supported IBX amide; oxidant;

D O I：

10.1016/j.tetlet.2003.10.077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel polymer supported IBX esters and amides were prepared in two steps, which were the coupling of 2-iodobenzoic acid to a hydroxy or amino polystyrene followed by activation of the intermediate product. These polymer supported reagents were tested as oxidants by the conversion of a series of alcohols to the corresponding aldehydes or ketones. We found that the polymer supported IBX amides displayed excellent oxidative activity, in that they oxidized benzyl alcohol to benzaldehyde completely within 1 h at an oxidant to alcohol ratio of 2 to 1. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：9251 / 9254

页数：4

共 22 条

[1] A MILD OXIDIZING REAGENT FOR ALCOHOLS AND 1,2-DIOLS - O-IODOXYBENZOIC ACID (IBX) IN DMSO [J].

FRIGERIO, M ;

SANTAGOSTINO, M .

TETRAHEDRON LETTERS, 1994, 35 (43) :8019-8022

[2] OXIDATION OF ALCOHOLS WITH O-IODOXYBENZOIC ACID (IBX) IN DMSO - A NEW INSIGHT INTO AN OLD HYPERVALENT IODINE REAGENT [J].

FRIGERIO, M ;

SANTAGOSTINO, M ;

SPUTORE, S ;

PALMISANO, G .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) :7272-7276

[3] A user-friendly entry to 2-iodoxybenzoic acid (IBX) [J].

Frigerio, M ;

Santagostino, M ;

Sputore, S .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4537-4538

[4] A facile route to a polymer-supported IBX reagent [J].

Lei, Z ;

Denecker, C ;

Jegasothy, S ;

Sherrington, DC ;

Slater, NKH ;

Sutherland, AJ .

TETRAHEDRON LETTERS, 2003, 44 (08) :1635-1637

[5]

LITVINOV DN, 2003, 225 AM CHEM SOC NAT

[6] Mild oxidation of alcohols with O-iodoxybenzoic acid (IBX) in ionic liquid 1-butyl-3-methyl-imidazolium chloride and water [J].

Liu, Z ;

Chen, ZC ;

Zheng, QG .

ORGANIC LETTERS, 2003, 5 (18) :3321-3323

[7] A simple and advantageous protocol for the oxidation of alcohols with, o-iodoxybenzoic acid (IBX) [J].

More, JD ;

Finney, NS .

ORGANIC LETTERS, 2002, 4 (17) :3001-3003

[8]

Mülbaier M, 2001, ANGEW CHEM INT EDIT, V40, P4393, DOI 10.1002/1521-3773(20011203)40:23<4393::AID-ANIE4393>3.0.CO

[9]

2-2

[10] A new method for the one-step synthesis of α,β-unsaturated carbonyl systems from saturated alcohols and carbonyl compounds [J].

Nicolaou, KC ;

Zhong, YL ;

Baran, PS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (31) :7596-7597

← 1 2 3 →