Transition metal-mediated oxidations utilizing monomeric iodosyl- and iodylarene species

被引：74
|
作者：
Yusubov, Mekhman S. [2 ,3 ]
Nemykin, Victor N. [1 ]
Zhdankin, Viktor V. [1 ]
机构：
[1] Univ Minnesota, Dept Chem & Biochem, Duluth, MN 55812 USA
[2] Siberian State Med Univ, Tomsk 634050, Russia
[3] Tomsk Polytech Univ, Tomsk 634050, Russia
来源：
TETRAHEDRON | 2010年 / 66卷 / 31期
基金：
美国国家科学基金会;
关键词：
Hypervalent iodine; Oxidation; Catalysis; Ruthenium; Porphyrins; HYPERVALENT IODINE REAGENTS; O-IODOXYBENZOIC ACID; CATALYZED OXIDATION; SELECTIVE OXIDATION; RUCL3-CATALYZED OXIDATION; AROMATIC HYDROXYLATION; SECONDARY ALCOHOLS; KINETIC RESOLUTION; COMPLEXES; PALLADIUM;
D O I：
10.1016/j.tet.2010.04.046
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Several transition metal-mediated oxidations using hypervalent iodine species are reported. A convenient procedure for preparation of iodylarenes via RuCl3-catalyzed oxidation of iodoarenes has been developed. This procedure allows the generation of highly reactive monomeric iodine(V) species, which are excellent oxidants toward alcohols and hydrocarbons in situ. A broad range of substrates can be oxidized to carbonyl compounds by a tandem catalytic system based on the Ru(III)-catalyzed reoxidation of ArIO to ArIO2 using Oxone (R) as oxidant. It was shown that electrophilic iodine(III) species, originating from oligomeric iodosylbenzene sulfate (PhIO)(3)SO3, are efficient oxygenating agents in catalytic oxidation of aromatic hydrocarbons in the presence of metalloporphyrin complexes. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5745 / 5752
页数：8
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