[2+2+2]-Cyclotrimerization of 1-Cyclopropyl-1,6-diynes with Alkynes: Formation of Cyclopropylarenes

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F16%3A10323245" target="_blank" >RIV/00216208:11310/16:10323245 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1002/adsc.201500851" target="_blank" >http://dx.doi.org/10.1002/adsc.201500851</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/adsc.201500851" target="_blank" >10.1002/adsc.201500851</a>

Jazyk výsledku

angličtina

Název v původním jazyce

[2+2+2]-Cyclotrimerization of 1-Cyclopropyl-1,6-diynes with Alkynes: Formation of Cyclopropylarenes

Popis výsledku v původním jazyce

Cyclotrimerization of 1-cyclopropyl-1,6-diynes with various terminal alkynes was tested under catalytic conditions using rhodium and ruthenium catalysts. We observed that the regioselectivity of the reaction, that is, formation of 1,2- r 1,3-regioisomers, was opposite for the two metals. For the ruthenium complex [Cp*Ru(cod)Cl]-catalyzed reactions the yields were in many cases high with a strong preference for the formation of 1,3-substituted regioisomers. In the case of catalysis by the rhodium complex [RhCl(PPh3)(3)], 1,2-substituted products were generally preferred, albeit the selectivity was often modest. However, by changing the ligand environment around the central rhodium atom the regioselectivity as well as yields of the products were significantly improved. For example, by using a combination of the rhodium complex [Rh(cod)(2)BF4] and 1,4-bis(diphenylphosphino)butane the regioselectivity was changed from 1: 1 to 1: 12 in favor of the 1,2-regioisomer. This catalytic system was also applied for synthesis of a substituted 4-cyclopropyl-3-hydroisobenzofuran-1-one that could serve as a potential intermediate for preparation of antihypertensive agents.

Název v anglickém jazyce

[2+2+2]-Cyclotrimerization of 1-Cyclopropyl-1,6-diynes with Alkynes: Formation of Cyclopropylarenes

Popis výsledku anglicky

Cyclotrimerization of 1-cyclopropyl-1,6-diynes with various terminal alkynes was tested under catalytic conditions using rhodium and ruthenium catalysts. We observed that the regioselectivity of the reaction, that is, formation of 1,2- r 1,3-regioisomers, was opposite for the two metals. For the ruthenium complex [Cp*Ru(cod)Cl]-catalyzed reactions the yields were in many cases high with a strong preference for the formation of 1,3-substituted regioisomers. In the case of catalysis by the rhodium complex [RhCl(PPh3)(3)], 1,2-substituted products were generally preferred, albeit the selectivity was often modest. However, by changing the ligand environment around the central rhodium atom the regioselectivity as well as yields of the products were significantly improved. For example, by using a combination of the rhodium complex [Rh(cod)(2)BF4] and 1,4-bis(diphenylphosphino)butane the regioselectivity was changed from 1: 1 to 1: 12 in favor of the 1,2-regioisomer. This catalytic system was also applied for synthesis of a substituted 4-cyclopropyl-3-hydroisobenzofuran-1-one that could serve as a potential intermediate for preparation of antihypertensive agents.

Druh

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

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

<a href="/cs/project/GA13-15915S" target="_blank" >GA13-15915S: Vývoj metod pro syntézu seskviterpenů založených na zirconocenové chemii</a><br>

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

Advanced Synthesis and Catalysis

ISSN

1615-4150

e-ISSN

—

Svazek periodika

358

Číslo periodika v rámci svazku

2

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

14

Strana od-do

254-267

Kód UT WoS článku

000371975800004

EID výsledku v databázi Scopus

2-s2.0-84957557367