General and selective homogeneous Ru-catalyzed transfer hydrogenation, deuteration, and methylation of functional compounds using methanol
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989100%3A27640%2F23%3A10252968" target="_blank" >RIV/61989100:27640/23:10252968 - isvavai.cz</a>
Result on the web
<a href="https://www.sciencedirect.com/science/article/pii/S0021951723002828?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0021951723002828?via%3Dihub</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.jcat.2023.06.035" target="_blank" >10.1016/j.jcat.2023.06.035</a>
Alternative languages
Result language
angličtina
Original language name
General and selective homogeneous Ru-catalyzed transfer hydrogenation, deuteration, and methylation of functional compounds using methanol
Original language description
Catalytic valorization of methanol in organic synthesis and energy technologies is interesting and important for both fundamental research and industrial applications. In particular, its utilization as hydrogen, deuterium and methyl sources for selective reduction and deuteration reactions as well as to access N-methylated products is highly desirable and can be considered as a potential methodology for the amplification of transfer hydrogenation and C1 chemistry. Here, we report homogeneous Ru-MACHO complex catalyzed transfer hydrogenation of different functionalized compounds such as ketones, aldehydes, alkynes, alkenes, imines, azobenzenes, and nitro compounds as well as deoxygenation of N-oxide derivatives employing methanol as an affordable hydrogen donor and solvent. This Ru-based strategy has been proven to be very convenient for the deuteration process to synthesize advanced deuterium-labelled compounds, including the gram-scale synthesis of deuterated pharmaceuticals such as d-Cloperastine, d-Buclizine, d-Diphendyarmine, d-Modafinil, and d-Adrafinil using CD3OD. In addition, the application of methanol as a C1 source for the preparation of N-methylated products is showcased. Finally, kinetic and mechanistic investigations for this Ru-catalyzed transfer hydrogenation and deuteration protocols have been performed. (C) 2023
Czech name
—
Czech description
—
Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10400 - Chemical sciences
Result continuities
Project
—
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Catalysis
ISSN
0021-9517
e-ISSN
1090-2694
Volume of the periodical
425
Issue of the periodical within the volume
425
Country of publishing house
US - UNITED STATES
Number of pages
20
Pages from-to
386-405
UT code for WoS article
001033838600001
EID of the result in the Scopus database
2-s2.0-85163821805