Literature DB >> 11817948

Mechanistic study of alcohol oxidation by the Pd(OAc)(2)/O(2)/DMSO catalyst system and implications for the development of improved aerobic oxidation catalysts.

Bradley A Steinhoff1, Shannon R Fix, Shannon S Stahl.   

Abstract

The Pd(OAc)2/O2/DMSO catalyst system displays impressive versatility in the aerobic oxidation of organic substrates, ranging from alcohols to olefins. This report details mechanistic insights into these reactions. Dimethyl sulfoxide (DMSO) plays no redox role in the chemistry, and kinetic experiments identify the turnover-limiting step as DMSO-promoted oxidation of palladium(0) by molecular oxygen. The "chemical oxidase" pathway characterized for this catalyst system holds great promise for the design of new aerobic oxidation reactions.

Entities:  

Mesh：

Substances：

Year:  2002        PMID： 11817948     DOI： 10.1021/ja016806w

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  22 in total

1.  Modular synthesis of 1,2-diamine derivatives by palladium-catalyzed aerobic oxidative cyclization of allylic sulfamides.

Authors:  Richard I McDonald; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2010-07-26       Impact factor: 15.336

2.  Recent advancements and challenges of palladium(II)-catalyzed oxidation reactions with molecular oxygen as the sole oxidant.

Authors:  Keith M Gligorich; Matthew S Sigman
Journal:  Chem Commun (Camb)       Date:  2009-05-14       Impact factor: 6.222

3.  Development and comparison of the substrate scope of Pd-catalysts for the aerobic oxidation of alcohols.

Authors:  Mitchell J Schultz; Steven S Hamilton; David R Jensen; Matthew S Sigman
Journal:  J Org Chem       Date:  2005-04-29       Impact factor: 4.354

4.  Synthesis of cyclic enones via direct palladium-catalyzed aerobic dehydrogenation of ketones.

Authors:  Tianning Diao; Shannon S Stahl
Journal:  J Am Chem Soc       Date:  2011-08-29       Impact factor: 15.419

5.  Diazafluorenone-Promoted Oxidation Catalysis: Insights into the Role of Bidentate Ligands in Pd-Catalyzed Aerobic Aza-Wacker Reactions.

Authors:  Paul B White; Jonathan N Jaworski; Geyunjian Harry Zhu; Shannon S Stahl
Journal:  ACS Catal       Date:  2016-03-11       Impact factor: 13.084

6.  Characterization of DMSO coordination to palladium(II) in solution and insights into the aerobic oxidation catalyst, Pd(DMSO)2(TFA)2.

Authors:  Tianning Diao; Paul White; Ilia Guzei; Shannon S Stahl
Journal:  Inorg Chem       Date:  2012-10-23       Impact factor: 5.165

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.  Asymmetric intermolecular boron Heck-type reactions via oxidative palladium(II) catalysis with chiral tridentate NHC-amidate-alkoxide ligands.

Authors:  Kyung Soo Yoo; Justin O'Neill; Satoshi Sakaguchi; Richard Giles; Joo Ho Lee; Kyung Woon Jung
Journal:  J Org Chem       Date:  2010-01-01       Impact factor: 4.354

9.  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

10.  Palladium-catalyzed method for the synthesis of carbazoles via tandem C-H functionalization and C-N bond formation.

Authors:  W C Peter Tsang; Rachel H Munday; Gordon Brasche; Nan Zheng; Stephen L Buchwald
Journal:  J Org Chem       Date:  2008-08-29       Impact factor: 4.354
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.