Role of the sulfonamide moiety of Ru(II) half-sandwich complexes in the asymmetric transfer hydrogenation of 3,4-dihydroisoquinolines

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F16%3A43901699" target="_blank" >RIV/60461373:22310/16:43901699 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388971:_____/16:00472351 RIV/61388963:_____/16:00472253

Výsledek na webu

<a href="http://dx.doi.org/10.1007/s11144-016-0991-z" target="_blank" >http://dx.doi.org/10.1007/s11144-016-0991-z</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1007/s11144-016-0991-z" target="_blank" >10.1007/s11144-016-0991-z</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Role of the sulfonamide moiety of Ru(II) half-sandwich complexes in the asymmetric transfer hydrogenation of 3,4-dihydroisoquinolines

Popis výsledku v původním jazyce

The role of the sulfonamide moiety of Noyori-Ikariya [Ru(II)Cl(eta (6)-p-cymene)(S,S)-(N-arylsulfonyl-DPEN)] (where DPEN = 1,2-diphenylethylene-1,2-diamine) half-sandwich complexes in the asymmetric transfer hydrogenation (ATH) of imines (1-methyl-3,4-dihydroisoquinoline and 6,7-dimethoxy-1-methyl-3,4-dihydroisoquinoline) was investigated. Nine complexes were synthesized and characterized, most of which have not been previously reported and a majority of the corresponding ligands (N-arylsulfonyl-DPEN) have not been described in imine ATH. The study demonstrates that the structure of the sulfonamide fragment strongly affects the catalytic activity. By monitoring the reaction kinetics, it was found that the reactivity of certain complexes was moderately enhanced and the enantioselectivity was affected as well, albeit to a lesser extent. No simple structure-activity pattern was found, suggesting that extensive screening experiments are necessary in order to obtain the optimal catalyst for a particular substrate. The study complements other previously reported works on structure-activity relationships concerning Ru(II)-catalyzed ATH by adding a new dimension of investigation.

Název v anglickém jazyce

Role of the sulfonamide moiety of Ru(II) half-sandwich complexes in the asymmetric transfer hydrogenation of 3,4-dihydroisoquinolines

Popis výsledku anglicky

The role of the sulfonamide moiety of Noyori-Ikariya [Ru(II)Cl(eta (6)-p-cymene)(S,S)-(N-arylsulfonyl-DPEN)] (where DPEN = 1,2-diphenylethylene-1,2-diamine) half-sandwich complexes in the asymmetric transfer hydrogenation (ATH) of imines (1-methyl-3,4-dihydroisoquinoline and 6,7-dimethoxy-1-methyl-3,4-dihydroisoquinoline) was investigated. Nine complexes were synthesized and characterized, most of which have not been previously reported and a majority of the corresponding ligands (N-arylsulfonyl-DPEN) have not been described in imine ATH. The study demonstrates that the structure of the sulfonamide fragment strongly affects the catalytic activity. By monitoring the reaction kinetics, it was found that the reactivity of certain complexes was moderately enhanced and the enantioselectivity was affected as well, albeit to a lesser extent. No simple structure-activity pattern was found, suggesting that extensive screening experiments are necessary in order to obtain the optimal catalyst for a particular substrate. The study complements other previously reported works on structure-activity relationships concerning Ru(II)-catalyzed ATH by adding a new dimension of investigation.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2016

Kód důvěrnosti údajů

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

Název periodika

Reaction Kinetics Mechanisms and Catalysis

ISSN

1878-5190

e-ISSN

—

Svazek periodika

118

Číslo periodika v rámci svazku

1

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

8

Strana od-do

215-222

Kód UT WoS článku

000376107700018

EID výsledku v databázi Scopus

2-s2.0-84965109607