Synthesis of highly fluorescent helical quinolizinium salts by a Rh-catalyzed cyclotrimerization/C-H activation sequence

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F25%3A00618283" target="_blank" >RIV/61388955:_____/25:00618283 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00216208:11310/25:10500096

Výsledek na webu

<a href="https://hdl.handle.net/11104/0365126" target="_blank" >https://hdl.handle.net/11104/0365126</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d4cc06512c" target="_blank" >10.1039/d4cc06512c</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of highly fluorescent helical quinolizinium salts by a Rh-catalyzed cyclotrimerization/C-H activation sequence

Popis výsledku v původním jazyce

A series of helical quinolizinium salts were prepared utilizing Rh-catalyzed [2+2+2]cyclotrimerization and C-H activation processes as the crucial synthetic steps. The cyclotrimerization of appropriately substituted diynes with trimethylsilylethyne under Rh-catalyzed conditions provided the 1-arylisoquinolines in up to 61% isolated yields. Their Rh-catalyzed C-H activation/annulation with various aryl and alkyl disubstituted alkynes gave rise to [7]-helical quinolizinium salts in high isolated yields (up to 93%). Enantioselective C-H activation was also tried with asymmetric induction up to 62% ee. The respective boron and platinum complexes of 1-arylisoquinolines were prepared as well. All prepared compounds exhibit fluorescence in the orange-red light region (606-682 nm) with Phi Fs 28-99%.

Název v anglickém jazyce

Synthesis of highly fluorescent helical quinolizinium salts by a Rh-catalyzed cyclotrimerization/C-H activation sequence

Popis výsledku anglicky

A series of helical quinolizinium salts were prepared utilizing Rh-catalyzed [2+2+2]cyclotrimerization and C-H activation processes as the crucial synthetic steps. The cyclotrimerization of appropriately substituted diynes with trimethylsilylethyne under Rh-catalyzed conditions provided the 1-arylisoquinolines in up to 61% isolated yields. Their Rh-catalyzed C-H activation/annulation with various aryl and alkyl disubstituted alkynes gave rise to [7]-helical quinolizinium salts in high isolated yields (up to 93%). Enantioselective C-H activation was also tried with asymmetric induction up to 62% ee. The respective boron and platinum complexes of 1-arylisoquinolines were prepared as well. All prepared compounds exhibit fluorescence in the orange-red light region (606-682 nm) with Phi Fs 28-99%.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

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

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2025

Kód důvěrnosti údajů

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

Název periodika

Chemical Communications

ISSN

1359-7345

e-ISSN

1364-548X

Svazek periodika

61

Číslo periodika v rámci svazku

24

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

4

Strana od-do

4662-4665

Kód UT WoS článku

001413400400001

EID výsledku v databázi Scopus

2-s2.0-85217453690