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research article

Tandem Hydroformylation-Aldol Condensation Reaction Enabled by Zn-MOF-74

Gaeumann, Patrick
•
Rohrbach, Thomas
•
Artiglia, Luca
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May 19, 2023
Chemistry-A European Journal

The tandem hydroformylation-aldol condensation (tandem HF-AC) reaction offers an efficient synthetic route to the synthesis of industrially relevant products. The addition of Zn-MOF-74 to the cobalt-catalyzed hydroformylation of 1-hexene enables tandem HF-AC under milder pressure and temperature conditions than the aldox process, where zinc salts are added to cobalt-catalyzed hydroformylation reactions to promote aldol condensation. The yield of the aldol condensation products increases by up to 17 times compared to that of the homogeneous reaction without MOF and up to 5 times compared to the aldox catalytic system. Both Co-2(CO)(8) and Zn-MOF-74 are required to significantly enhance the activity of the catalytic system. Density functional theory simulations and Fourier-transform infrared experiments show that heptanal, the product of hydroformylation, adsorbs on the open metal site (OMS) of Zn-MOF-74, thereby increasing the electrophilic character of the carbonyl carbon atom and facilitating the condensation.

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Type
research article
DOI
10.1002/chem.202300939
Web of Science ID

WOS:000991482300001

Author(s)
Gaeumann, Patrick
•
Rohrbach, Thomas
•
Artiglia, Luca
•
Ongari, Daniele  
•
Smit, Berend  
•
van Bokhoven, Jeroen A.
•
Ranocchiari, Marco
Date Issued

2023-05-19

Publisher

WILEY-V C H VERLAG GMBH

Published in
Chemistry-A European Journal
Subjects

Chemistry, Multidisciplinary

•

Chemistry

•

adsorption

•

aldol reaction

•

cobalt

•

hydroformylation

•

metal-organic framework

•

metal-organic frameworks

•

hydrogen storage

•

m-2(dobdc) m

•

x-ray

•

catalysts

•

alkenes

•

co2

•

ni

•

olefins

Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSMO  
Available on Infoscience
June 5, 2023
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/197980
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