Synthesis of α-ester-β-keto peroxides via iron-catalyzed carbonylation-peroxidation of α,β-unsaturated esters

被引：49

作者：

Liu, Kaisheng ^{[1
]}

Li, Yuanming ^{[1
]}

Zheng, Xiaojian ^{[1
]}

Liu, Weiping ^{[1
]}

Li, Zhiping ^{[1
,2
]}

机构：

[1] Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China

[2] China Univ Petr, State Key Lab Heavy Oil Proc, Beijing 102249, Peoples R China

来源：

TETRAHEDRON | 2012年 / 68卷 / 50期

基金：

美国国家科学基金会;

关键词：

Iron catalysis; Organic peroxides; Peroxidation; Carbonylation; Alkene di-functionalization; TERT-BUTYL HYDROPEROXIDE; RADICAL REACTIONS; MIXED PEROXIDES; CHEMISTRY; OXIDATION; ALKENES; ALDEHYDES;

D O I：

10.1016/j.tet.2012.09.110

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and practical method for the synthesis of alpha-ester-beta-keto peroxides has been achieved by iron-catalyzed three-component reactions of alkenes, aldehydes, and TBHP. A wide variety of functionalized organic peroxides were synthesized efficiently and selectively. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：10333 / 10337

页数：5

共 49 条

[1]

Adam W, 2000, PEROXIDE CHEM

[2] HYDROPEROXIDES AS PSEUDOHALIDES - OXIDATION, OXIDATIVE ALKYLATION, ACYLATION AND ARYLATION OF ACRYLONITRILE [J].

ARANEO, S ;

FONTANA, F ;

MINISCI, F ;

RECUPERO, F ;

SERRI, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (14) :1399-1400

[3] Gif chemistry: The present situation [J].

Barton, DHR .

TETRAHEDRON, 1998, 54 (22) :5805-5817

[4] Iron-catalyzed reactions in organic synthesis [J].

Bolm, C ;

Legros, J ;

Le Paih, J ;

Zani, L .

CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254

[5] Ingold-Fischer ''persistent radical effect'', solvent effect, and metal salt oxidation of carbon-centered radicals in the synthesis of mixed peroxides from tert-butyl hydroperoxide [J].

Bravo, A ;

Bjorsvik, HR ;

Fontana, F ;

Liguori, L ;

Minisci, F .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :3849-3857

[6] Chemistry of acyl radicals [J].

Chatgilialoglu, C ;

Crich, D ;

Komatsu, M ;

Ryu, I .

CHEMICAL REVIEWS, 1999, 99 (08) :1991-2069

[7]

Chudasama V, 2010, NAT CHEM, V2, P592, DOI [10.1038/NCHEM.685, 10.1038/nchem.685]

[8] Iron-catalysed carbon-heteroatom and heteroatom-heteroatom bond forming processes [J].

Correa, Arkaitz ;

Mancheno, Olga Garcia ;

Bolm, Carsten .

CHEMICAL SOCIETY REVIEWS, 2008, 37 (06) :1108-1117

[9] Oxidations of iron(II)/(III) by hydrogen peroxide: from aquo to enzyme [J].

Dunford, HB .

COORDINATION CHEMISTRY REVIEWS, 2002, 233 :311-318

[10] Sustainable metal catalysis with iron: From rust to a rising star? [J].

Enthaler, Stephan ;

Junge, Kathrin ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (18) :3317-3321

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