Selenium Catalyzed Oxidation of Aldehydes: Green Synthesis of Carboxylic Acids and Esters

被引：86

作者：

Sancineto, Luca ^{[1
]}

Tidei, Caterina ^{[1
]}

Bagnoli, Luana ^{[1
]}

Marini, Francesca ^{[1
]}

Lenardao, Eder J. ^{[2
]}

Santi, Claudio ^{[1
]}

机构：

[1] Univ Perugia, Dept Pharmaceut Sci, Grp Catalysis & Organ Green Chem, I-06100 Perugia, Italy

[2] Univ Fed Pelotas, CCQFA, LASOL, BR-96010900 Pelotas, Brazil

来源：

MOLECULES | 2015年 / 20卷 / 06期

基金：

瑞典研究理事会;

关键词：

aldehydes; oxidation; selenium; catalysis; carboxylic acids; esters; hydrogen peroxide; green chemistry; HYDROGEN-PEROXIDE; SELECTIVE OXIDATION; AROMATIC-ALDEHYDES; EFFICIENT SYSTEM; PRIMARY ALCOHOLS; METHYL-ESTERS; ESTERIFICATION; KETONES; WATER; DIHYDROXYLATION;

D O I：

10.3390/molecules200610496

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The stoichiometric use of hydrogen peroxide in the presence of a selenium-containing catalyst in water is here reported as a new ecofriendly protocol for the synthesis of variously functionalized carboxylic acids and esters. The method affords the desired products in good to excellent yields under very mild conditions starting directly from commercially available aldehydes. Using benzaldehyde as a prototype the gram scale synthesis of benzoic acid is described, in which the aqueous medium and the catalyst could be recycled at last five times while achieving an 87% overall yield.

引用

页码：10496 / 10510

页数：15

共 52 条

[1] KMNO4 REVISITED - OXIDATION OF ALDEHYDES TO CARBOXYLIC-ACIDS IN THE TERT-BUTYL ALCOHOL AQUEOUS NAH2PO4 SYSTEM [J].

ABIKO, A ;

ROBERTS, JC ;

TAKEMASA, T ;

MASAMUNE, S .

TETRAHEDRON LETTERS, 1986, 27 (38) :4537-4540

[2] Imidazolium-containing diselenides for catalytic oxidations with hydrogen peroxide and sodium bromide in aqueous solutions [J].

Alberto, Eduardo E. ;

Braga, Antonio L. ;

Detty, Michael R. .

TETRAHEDRON, 2012, 68 (51) :10476-10481

[3] Pd/C and NaBH4 in Basic Aqueous Alcohol: An Efficient System for an Environmentally Benign Oxidation of Alcohols [J].

An, Gwangil ;

Ahn, Hyunseok ;

De Castro, Kathlia A. ;

Rhee, Hakjune .

SYNTHESIS-STUTTGART, 2010, (03) :477-485

[4] Hydrolysis of alkenyl esters and ethers catalyzed by metal complexes [J].

Aoyama, H ;

Tokunaga, M ;

Hiraiwa, S ;

Shirogane, Y ;

Obora, Y ;

Tsuji, Y .

ORGANIC LETTERS, 2004, 6 (04) :509-512

[5] "On-Water" Michael-Type Addition Reactions Promoted by PhSeZnCl [J].

Battistelli, Benedetta ;

Lorenzo, Testaferri ;

Tiecco, Marcello ;

Santi, Claudio .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (10) :1848-1851

[6] Selenium(IV) oxide catalyzed oxidation of aldehydes to carboxylic acids with hydrogen peroxide [J].

Brzaszcz, M ;

Kloc, K ;

Maposah, M ;

Mlochowski, J .

SYNTHETIC COMMUNICATIONS, 2000, 30 (24) :4425-4434

[7]

Cardona F., 2015, TRANSITION METAL

[8] Ruthenium-catalyzed oxidation of alkenes, alkynes, and alcohols to organic acids with aqueous hydrogen peroxide [J].

Che, Chi-Ming ;

Yip, Wing-Ping ;

Yu, Wing-Yiu .

CHEMISTRY-AN ASIAN JOURNAL, 2006, 1 (03) :453-458

[9] On the Role of CO2 in NHC-Catalyzed Oxidation of Aldehydes [J].

Chiang, Pei-Chen ;

Bode, Jeffrey W. .

ORGANIC LETTERS, 2011, 13 (09) :2422-2425

[10] CATALYTIC-OXIDATION OF ALDEHYDES TO CARBOXYLIC-ACIDS WITH HYDROGEN-PEROXIDE AS OXIDANT [J].

CHOI, JK ;

CHANG, YK ;

HONG, SY .

TETRAHEDRON LETTERS, 1988, 29 (16) :1967-1970

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