General and selective homogeneous Ru-catalyzed transfer hydrogenation, deuteration, and methylation of functional compounds using methanol

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

General and selective homogeneous Ru-catalyzed transfer hydrogenation, deuteration, and methylation of functional compounds using methanol

Popis výsledku v původním jazyce

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

Název v anglickém jazyce

General and selective homogeneous Ru-catalyzed transfer hydrogenation, deuteration, and methylation of functional compounds using methanol

Popis výsledku anglicky

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

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10400 - Chemical sciences

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2023

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of Catalysis

ISSN

0021-9517

e-ISSN

1090-2694

Svazek periodika

425

Číslo periodika v rámci svazku

425

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

20

Strana od-do

386-405

Kód UT WoS článku

001033838600001

EID výsledku v databázi Scopus

2-s2.0-85163821805