Literature DB >> 12234207

Green, catalytic oxidations of alcohols.

Roger A Sheldon1, Isabel W C E Arends, Gerd-Jan Ten Brink, Arné Dijksman.   

Abstract

Three methods are described, in the context of the guiding principles of green chemistry, for the catalytic oxidation of alcohols. The first employs a recyclable oligomeric TEMPO catalyst (PIPO) and sodium hypochlorite as the oxidant in a bromide-free and chlorinated hydrocarbon solvent-free system. The second involves a ruthenium/TEMPO catalyst and oxygen as the oxidant. The third consists of a recyclable water-soluble palladium-diamine complex in conjunction with air as the oxidant in an aqueous biphasic system. The mechanisms of the ruthenium/TEMPO- and palladium-catalyzed oxidations are discussed, and the mechanism of the former is compared with that of the analogous copper/TEMPO catalyst.

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Year:  2002        PMID： 12234207     DOI： 10.1021/ar010075n

Source DB:  PubMed          Journal:  Acc Chem Res        ISSN： 0001-4842            Impact factor:   22.384


  48 in total

1.  Allylic C-H acetoxylation with a 4,5-diazafluorenone-ligated palladium catalyst: a ligand-based strategy to achieve aerobic catalytic turnover.

Authors:  Alison N Campbell; Paul B White; Ilia A Guzei; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2010-11-03       Impact factor: 15.419

Review 2.  Thermochemistry of proton-coupled electron transfer reagents and its implications.

Authors:  Jeffrey J Warren; Tristan A Tronic; James M Mayer
Journal:  Chem Rev       Date:  2010-10-06       Impact factor: 60.622

3.  Cu/Nitroxyl Catalyzed Aerobic Oxidation of Primary Amines into Nitriles at Room Temperature.

Authors:  Jinho Kim; Shannon S Stahl
Journal:  ACS Catal       Date:  2013-07-05       Impact factor: 13.084

4.  Folded biomimetic oligomers for enantioselective catalysis.

Authors:  Galia Maayan; Michael D Ward; Kent Kirshenbaum
Journal:  Proc Natl Acad Sci U S A       Date:  2009-08-10       Impact factor: 11.205

5.  Mechanism of alcohol oxidation mediated by copper(II) and nitroxyl radicals.

Authors:  Bradford L Ryland; Scott D McCann; Thomas C Brunold; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2014-08-14       Impact factor: 15.419

6.  Copper/TEMPO-Catalyzed Aerobic Alcohol Oxidation: Mechanistic Assessment of Different Catalyst Systems.

Authors:  Jessica M Hoover; Bradford L Ryland; Shannon S Stahl
Journal:  ACS Catal       Date:  2013-11-01       Impact factor: 13.084

7.  The palladium-catalyzed aerobic kinetic resolution of secondary alcohols: reaction development, scope, and applications.

Authors:  David C Ebner; Jeffrey T Bagdanoff; Eric M Ferreira; Ryan M McFadden; Daniel D Caspi; Raissa M Trend; Brian M Stoltz
Journal:  Chemistry       Date:  2009-12-07       Impact factor: 5.236

8.  Elucidating the significance of beta-hydride elimination and the dynamic role of acid/base chemistry in a palladium-catalyzed aerobic oxidation of alcohols.

Authors:  Jaime A Mueller; Christopher P Goller; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2004-08-11       Impact factor: 15.419

9.  Mechanism of copper(I)/TEMPO-catalyzed aerobic alcohol oxidation.

Authors:  Jessica M Hoover; Bradford L Ryland; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2013-01-31       Impact factor: 15.419

10.  Synthesis of 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate and 4-acetamido-(2,2,6,6-tetramethyl-piperidin-1-yl)oxyl and their use in oxidative reactions.

Authors:  Michael A Mercadante; Christopher B Kelly; James M Bobbitt; Leon J Tilley; Nicholas E Leadbeater
Journal:  Nat Protoc       Date:  2013-03-07       Impact factor: 13.491
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