Organocatalytic Dakin Oxidation by Nucleophilic Flavin Catalysts

被引：66

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

[41]

2-S

[42] FLAVIN-CATALYZED OXIDATION OF AMINES AND SULFUR-COMPOUNDS WITH HYDROGEN-PEROXIDE [J].

MURAHASHI, SI ;

ODA, T ;

MASUI, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) :5002-5003

[43] DIOXYGEN TRANSFER FROM 4A-HYDROPEROXYFLAVIN ANION .2. OXYGEN-TRANSFER TO THE 10 POSITION OF 9-HYDROXYPHENANTHRENE ANIONS AND TO 3,5-DI-TERT-BUTYLCATECHOL ANION [J].

MUTO, S ;

BRUICE, TC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (13) :4472-4480

[44] Improved Density Functional Description of the Electrochemistry and Structure-Property Descriptors of Substituted Flavins [J].

North, Michael A. ;

Bhattacharyya, Sudeep ;

Truhlar, Donald G. .

JOURNAL OF PHYSICAL CHEMISTRY B, 2010, 114 (46) :14907-14915

[45] Density Functional Theory Analysis of Dichloromethane and Hydrogen Interaction with Pd Clusters: First Step to Simulate Catalytic Hydrodechlorination [J].

Omar, Salama ;

Palomar, Jose ;

Gomez-Sainero, Luisa M. ;

Alvarez-Montero, Maria A. ;

Martin-Martinez, Maria ;

Rodriguez, Juan J. .

JOURNAL OF PHYSICAL CHEMISTRY C, 2011, 115 (29) :14180-14192

[46] 8-CHLOROALLOXAZINE, NEW DIURETIC - SYNTHESIS AND STRUCTURE [J].

PETERING, HG ;

VANGIESS.GJ .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (08) :2818-&

[47] Quantum Mechanical/Molecular Mechanical Study on the Mechanism of the Enzymatic Baeyer-Villiger Reaction [J].

Polyak, Iakov ;

Reetz, Manfred T. ;

Thiel, Walter .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (05) :2732-2741

[48] Chemo-enzymatic Baeyer-Villiger oxidation of cyclopentanone and substituted cyclopentanones [J].

Rios, Maria Yolanda ;

Salazar, Enrique ;

Olivo, Horacio F. .

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2008, 54 (3-4) :61-66

[49] Exploring the biocatalytic scope of a bacterial flavin-containing monooxygenase [J].

Rioz-Martinez, Ana ;

Kopacz, Malgorzata ;

de Gonzalo, Gonzalo ;

Pazmino, Daniel E. Torres ;

Gotor, Vicente ;

Fraaije, Marco W. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (05) :1337-1341

[50] Hydrogen peroxide/boric acid: An efficient system for oxidation of aromatic aldehydes and ketones to phenols [J].

Roy, A ;

Reddy, KR ;

Mohanta, PK ;

Ila, H ;

Junjappa, H .

SYNTHETIC COMMUNICATIONS, 1999, 29 (21) :3781-3791

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