Literature DB >> 27595612

Harnessing the Power of the Water-Gas Shift Reaction for Organic Synthesis.

Andrea Ambrosi1, Scott E Denmark2.   

Abstract

Since its original disn class="Chemical">covery over a century ago, the water-gas shift reaction (WGSR) has played a crucial role in industrial chemistry, providing a source of H2 to feed fundamental industrial transformations such as the Haber-Bosch synthesis of ammonia. Although the production of hydrogen remains nowadays the major application of the WGSR, the advent of homogeneous catalysis in the 1970s marked the beginning of a synergy between WGSR and organic chemistry. Thus, the reducing power provided by the CO/H2 O couple has been exploited in the synthesis of fine chemicals; not only hydrogenation-type reactions, but also catalytic processes that require a reductive step for the turnover of the catalytic cycle. Despite the potential and unique features of the WGSR, its applications in organic synthesis remain largely underdeveloped. The topic will be critically reviewed herein, with the expectation that an increased awareness may stimulate new, creative work in the area.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbon monoxide; heterogeneous catalysis; homogeneous catalysis; reduction; transition metals

Year:  2016        PMID: 27595612      PMCID: PMC6201252          DOI: 10.1002/anie.201601803

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  41 in total

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Journal:  J Phys Chem A       Date:  2012-02-23       Impact factor: 2.781

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Authors:  Pavel N Kolesnikov; Dmitry L Usanov; Evgeniya A Barablina; Victor I Maleev; Denis Chusov
Journal:  Org Lett       Date:  2014-09-16       Impact factor: 6.005

3.  Ethene hydroformylation with CO/H2O: nucleophilic attack by water on to a terminal CO of a Ru(II) acylcarbonyl complex.

Authors:  Giuseppe Fachinetti; Tiziana Funaioli; Fabio Marchetti
Journal:  Chem Commun (Camb)       Date:  2005-06-21       Impact factor: 6.222

4.  Rhodium-catalyzed reductive allylation of conjugated aldehydes with allyl acetate.

Authors:  Maksym Vasylyev; Howard Alper
Journal:  J Org Chem       Date:  2010-04-16       Impact factor: 4.354

5.  Theoretical study of the gas-phase Fe(CO)5 catalyzed water gas shift reaction: a new mechanism proposed.

Authors:  Susan E Barrows
Journal:  Inorg Chem       Date:  2004-12-27       Impact factor: 5.165

Review 6.  Gold catalysts for pure hydrogen production in the water-gas shift reaction: activity, structure and reaction mechanism.

Authors:  Robbie Burch
Journal:  Phys Chem Chem Phys       Date:  2006-10-02       Impact factor: 3.676

7.  A novel gold-catalyzed chemoselective reduction of alpha,beta-unsaturated aldehydes using CO and H2O as the hydrogen source.

Authors:  Lin He; Feng-Jiao Yu; Xia-Bing Lou; Yong Cao; He-Yong He; Kang-Nian Fan
Journal:  Chem Commun (Camb)       Date:  2010-01-28       Impact factor: 6.222

8.  The activation of gold and the water-gas shift reaction: insights from studies with model catalysts.

Authors:  José A Rodriguez; Sanjaya D Senanayake; Dario Stacchiola; Ping Liu; Jan Hrbek
Journal:  Acc Chem Res       Date:  2013-11-06       Impact factor: 22.384

9.  Efficient and exceptionally selective semireduction of alkynes using a supported gold catalyst under a CO atmosphere.

Authors:  Shu-Shuang Li; Xiang Liu; Yong-Mei Liu; He-Yong He; Kang-Nian Fan; Yong Cao
Journal:  Chem Commun (Camb)       Date:  2014-05-30       Impact factor: 6.222

10.  Gold atoms stabilized on various supports catalyze the water-gas shift reaction.

Authors:  Maria Flytzani-Stephanopoulos
Journal:  Acc Chem Res       Date:  2013-11-22       Impact factor: 22.384

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  7 in total

1.  Catalytic Nucleophilic Allylation Driven by the Water-Gas Shift Reaction.

Authors:  Scott E Denmark; Zachery D Matesich; Son T Nguyen; Selena Milicevic Sephton
Journal:  J Org Chem       Date:  2017-12-08       Impact factor: 4.354

2.  Improving the Performance of Supported Ionic Liquid Phase Catalysts for the Ultra-Low-Temperature Water Gas Shift Reaction Using Organic Salt Additives.

Authors:  Patrick Wolf; Christian R Wick; Julian Mehler; Dominik Blaumeiser; Simon Schötz; Tanja Bauer; Jörg Libuda; David Smith; Ana-Sunčana Smith; Marco Haumann
Journal:  ACS Catal       Date:  2022-04-27       Impact factor: 13.700

3.  Palladium/Rhodium Cooperative Catalysis for the Production of Aryl Aldehydes and Their Deuterated Analogues Using the Water-Gas Shift Reaction.

Authors:  Malek Y S Ibrahim; Scott E Denmark
Journal:  Angew Chem Int Ed Engl       Date:  2018-07-17       Impact factor: 15.336

4.  High performance of a cobalt-nitrogen complex for the reduction and reductive coupling of nitro compounds into amines and their derivatives.

Authors:  Peng Zhou; Liang Jiang; Fan Wang; Kejian Deng; Kangle Lv; Zehui Zhang
Journal:  Sci Adv       Date:  2017-02-17       Impact factor: 14.136

5.  Dynamic structure of active sites in ceria-supported Pt catalysts for the water gas shift reaction.

Authors:  Yuanyuan Li; Matthew Kottwitz; Joshua L Vincent; Michael J Enright; Zongyuan Liu; Lihua Zhang; Jiahao Huang; Sanjaya D Senanayake; Wei-Chang D Yang; Peter A Crozier; Ralph G Nuzzo; Anatoly I Frenkel
Journal:  Nat Commun       Date:  2021-02-10       Impact factor: 14.919

6.  Deoxygenation of Epoxides with Carbon Monoxide.

Authors:  Theo Maulbetsch; Eva Jürgens; Doris Kunz
Journal:  Chemistry       Date:  2020-07-23       Impact factor: 5.236

7.  Cascade Synthesis of Pyrroles from Nitroarenes with Benign Reductants Using a Heterogeneous Cobalt Catalyst.

Authors:  Pavel Ryabchuk; Thomas Leischner; Carsten Kreyenschulte; Anke Spannenberg; Kathrin Junge; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-31       Impact factor: 16.823

  7 in total

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