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

Since its original discovery 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 no...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-09, Vol.55 (40), p.12164-12189
Main Authors: Ambrosi, Andrea, Denmark, Scott E.
Format: Article
Language:English
Subjects:
Ammonia
carbon monoxide
Catalysis
Chemical bonds
Chemical synthesis
Chemicals
Chemistry
Fine chemicals
heterogeneous catalysis
homogeneous catalysis
Hydrogen
Hydrogen production
Hydrogen storage
Hydrogenation
Organic chemistry
reduction
Reviews
Shift reaction
Transformations
transition metals
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Summary:Since its original discovery 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/H2O 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. New directions for a classic: In addition to its fundamental role in the production of hydrogen, the water‐gas shift reaction has found application in a multitude of reductive transformations in organic synthesis. These include hydrogenation‐type reactions, as well as catalytic, overall‐reductive processes wherein the CO/H2O couple can act as the terminal reductant.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201601803