Mechanistic investigation of the gold-catalyzed aerobic oxidation of aldehydes: added insight from Hammett studies and isotopic labelling experiments

被引：58

作者：

Fristrup, Peter ^{[1
]}

Johansen, Louise Bahn ^{[1
]}

Christensen, Claus Hviid ^{[1
]}

机构：

[1] Tech Univ Denmark, Ctr Sustainable & Green Chem, DK-2800 Lyngby, Denmark

来源：

CHEMICAL COMMUNICATIONS | 2008年 / 24期

关键词：

D O I：

10.1039/b803270j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The gold-catalyzed aerobic oxidation of aldehydes proceeds through development of a partial negative charge and has a significant kinetic isotope effect (k(H)/k(D) = 2.8-2.9), which illustrates that activation of the C-H bond takes place in the rate-determining step.

引用

页码：2750 / 2752

页数：3

共 26 条

[1] A collaborative effect between gold and a support induces the selective oxidation of alcohols [J].

Abad, A ;

Concepción, P ;

Corma, A ;

García, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (26) :4066-4069

[2]

Bond G.C., 2006, CATALYSIS GOLD, DOI 10.1007/bf03215560

[3] The structure of catalytically active gold on titania [J].

Chen, MS ;

Goodman, DW .

SCIENCE, 2004, 306 (5694) :252-255

[4] Formation of acetic acid by aqueous-phase oxidation of ethanol with air in the presence of a heterogeneous gold catalyst [J].

Christensen, Claus H. ;

Jorgensen, Betina ;

Rass-Hansen, Jeppe ;

Egeblad, Kresten ;

Madsen, Robert ;

Klitgaard, Soren K. ;

Hansen, Stine M. ;

Hansen, Mike R. ;

Andersen, Hans C. ;

Riisager, Anders .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (28) :4648-4651

[5] Aerobic oxidation of glucose with gold catalyst: Hydrogen peroxide as intermediate and reagent [J].

Comotti, M ;

Della Pina, C ;

Falletta, E ;

Rossi, M .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (03) :313-316

[6] Gold supported on a mesoporous CeO2 matrix as an efficient catalyst in the selective aerobic oxidation of aldehydes in the liquid phase [J].

Corma, A ;

Domine, ME .

CHEMICAL COMMUNICATIONS, 2005, (32) :4042-4044

[7] Chemical routes for the transformation of biomass into chemicals [J].

Corma, Avelino ;

Iborra, Sara ;

Velty, Alexandra .

CHEMICAL REVIEWS, 2007, 107 (06) :2411-2502

[8] METHYLENECYCLOPROPANE REARRANGEMENT AS A PROBE FOR FREE-RADICAL SUBSTITUENT EFFECTS - SIGMA.-VALUES FOR COMMONLY ENCOUNTERED CONJUGATING AND ORGANOMETALLIC GROUPS [J].

CREARY, X ;

MEHRSHEIKHMOHAMMADI, ME ;

MCDONALD, S .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (15) :3254-3263

[9] Gold in a metallic divided state - From Faraday to present-day nanoscience [J].

Edwards, Peter P. ;

Thomas, John Meurig .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5480-5486

[10] Solvent-free oxidation of primary alcohols to aldehydes using Au-Pd/TiO2 catalysts [J].

Enache, DI ;

Edwards, JK ;

Landon, P ;

Solsona-Espriu, B ;

Carley, AF ;

Herzing, AA ;

Watanabe, M ;

Kiely, CJ ;

Knight, DW ;

Hutchings, GJ .

SCIENCE, 2006, 311 (5759) :362-365

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