Organocatalytic Dakin Oxidation by Nucleophilic Flavin Catalysts

被引：65

作者：

Chen, Shuai ^{[1
]}

Hossein, Mohammad S. ^{[1
]}

Foss, Frank W., Jr. ^{[1
]}

机构：

[1] Univ Texas Arlington, Dept Chem & Biochem, Arlington, TX 76019 USA

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 11期

基金：

美国国家科学基金会;

关键词：

BAEYER-VILLIGER OXIDATION; OXYGEN-ATOM TRANSFER; HYDROGEN-PEROXIDE; MOLECULAR-OXYGEN; ALKYL HYDROPEROXIDES; AROMATIC-ALDEHYDES; CRYSTAL-STRUCTURE; EFFICIENT; AMINES; MONOOXYGENASES;

D O I：

10.1021/ol3010326

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Flavin catalysts perform the first organocatalytic Dakin oxidation of electron-rich arylaldehydes to phenols under mild, basic conditions. Catechols are readily prepared, and the oxidation of 2-hydroxyacetophenone was achieved. Aerobic oxidation is displayed in the presence of Zn(0) as a reducing agent. This reactivity broadens the scope of biomimetic flavin catalysis in the realm of nucleophilic oxidations, providing a framework for mechanistic investigations for related oxidations, such as the Baeyer-Villiger oxidation and Weitz-Scheffer epoxidation.

引用

页码：2806 / 2809

页数：4

共 59 条

[11] Mild and efficient flavin-catalyzed H2O2 oxidation of tertiary amines to amine N-oxides [J].

Bergstad, K ;

Bäckvall, JE .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19) :6650-6655

[12] Oxidation of aromatic aldehydes and ketones by H2O2/CH3ReO3 in ionic liquids:: a catalytic efficient reaction to achieve dihydric phenols [J].

Bernini, R ;

Coratti, A ;

Provenzano, G ;

Fabrizi, G ;

Tofani, D .

TETRAHEDRON, 2005, 61 (07) :1821-1825

[13] Dimethyl carbonate:: an environmentally friendly solvent for hydrogen peroxide (H2O2)/methyltrioxorhenium (CH3ReO3, MTO) catalytic oxidations [J].

Bernini, Roberta ;

Mincione, Enrico ;

Barontini, Maurizio ;

Crisante, Fernanda ;

Fabrizi, Giancarlo ;

Gambacorta, Augusto .

TETRAHEDRON, 2007, 63 (29) :6895-6900

[14] MONOOXYGEN DONATION POTENTIAL OF 4A-HYDROPEROXYFLAVINS AS COMPARED WITH THOSE OF A PERCARBOXYLIC ACID AND OTHER HYDROPEROXIDES - MONOOXYGEN DONATION TO OLEFIN, TERTIARY AMINE, ALKYL SULFIDE, AND IODIDE-ION [J].

BRUICE, TC ;

NOAR, JB ;

BALL, SS ;

VENKATARAM, UV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (08) :2452-2463

[15] MECHANISMS OF FLAVIN CATALYSIS [J].

BRUICE, TC .

ACCOUNTS OF CHEMICAL RESEARCH, 1980, 13 (08) :256-262

[16] Neutral versus charged species in enzyme catalysis. Classical and free energy barriers for oxygen atom transfer from C4a-hydroperoxyflavin to dimethyl sulfide [J].

Canepa, C ;

Bach, RD ;

Dmitrenko, O .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (24) :8653-8661

[17] Improved solvent-free Dakin oxidation protocol [J].

da Silva, Emerson Teixeira ;

Camara, Celso Amorim ;

Antunes, O. A. C. ;

Barreiro, Eliezer J. ;

Fraga, Carlos A. M. .

SYNTHETIC COMMUNICATIONS, 2008, 38 (05) :784-788

[18] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].

GAO, Y ;

HANSON, RM ;

KLUNDER, JM ;

KO, SY ;

MASAMUNE, H ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780

[19]

GHISLA S, 1973, LIEBIGS ANN CHEM, P1388

[20] The Total Synthesis of (±)-Fumimycin [J].

Gross, Patrick J. ;

Braese, Stefan .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (42) :12660-12667

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