Iron-Catalyzed Carbonylation-Peroxidation of Alkenes with Aldehydes and Hydroperoxides

被引：295

作者：

Liu, Weiping ^{[1
]}

Li, Yuanming ^{[1
]}

Liu, Kaisheng ^{[1
]}

Li, Zhiping ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 28期

基金：

美国国家科学基金会;

关键词：

C-C BOND; RADICAL CHEMISTRY; EPOXIDATION; OXIDATION; CARBON; FUNCTIONALIZATION; HYDROACYLATION; ACTIVATION; ESTERS; SCOPE;

D O I：

10.1021/ja204226n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A three-component reaction of alkenes, aldehydes, and hydroperoxides catalyzed by FeCl2 to beta-peroxy ketones has been achieved. This three-component reaction can be also applied to the synthesis of a-carbonyl epoxides, through either a stepwise base-induced epoxidation of the separated beta-peroxy ketone products or a one-pot process by simply adding base to the reaction mixture after the completion of the three-component reaction.

引用

页码：10756 / 10759

页数：4

共 69 条

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

Barton, DHR .

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

[2] C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].

Beccalli, Egle M. ;

Broggini, Gianluigi ;

Martinelli, Michela ;

Sottocornola, Silvia .

CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365

[3] Catalytic Markovnikov and anti-Markovnikov functionalization of alkenes and alkynes: Recent developments and trends [J].

Beller, M ;

Seayad, J ;

Tillack, A ;

Jiao, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3368-3398

[4] A Novel Iron-Catalyzed Decarboxylative Csp3-Csp2 Coupling of Proline Derivatives and Naphthol [J].

Bi, Hai-Peng ;

Chen, Wen-Wen ;

Liang, Yong-Min ;

Li, Chao-Jun .

ORGANIC LETTERS, 2009, 11 (15) :3246-3249

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

Bolm, C ;

Legros, J ;

Le Paih, J ;

Zani, L .

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

[6] 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

[7] Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds [J].

Brennfuehrer, Anne ;

Neumann, Helfried ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4114-4133

[8] Multicatalytic Synthesis of α-Pyrrolidinyl Ketones via a Tandem Palladium(II)/Indium(III)-Catalyzed Aminochlorocarbonylation/Friedel-Crafts Acylation Reaction [J].

Cernak, Tim A. ;

Lambert, Tristan H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (09) :3124-+

[9] Chemistry of acyl radicals [J].

Chatgilialoglu, C ;

Crich, D ;

Komatsu, M ;

Ryu, I .

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

[10] Isotope effects and the mechanism of epoxidation of cyclohexenone with tert-butyl hydroperoxide [J].

Christian, Chad F. ;

Takeya, Tetsuya ;

Szymanski, Michael J. ;

Singleton, Daniel A. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) :6183-6189

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