Switchable cyclopalladation of substrates containing two directing groups: on the way to non-symmetrical [2.2]-dipalladaparacyclophanes

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F23%3A39920564" target="_blank" >RIV/00216275:25310/23:39920564 - isvavai.cz</a>

Výsledek na webu

<a href="https://pubs.rsc.org/en/content/articlelanding/2023/DT/D3DT02019C" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2023/DT/D3DT02019C</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d3dt02019c" target="_blank" >10.1039/d3dt02019c</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Switchable cyclopalladation of substrates containing two directing groups: on the way to non-symmetrical [2.2]-dipalladaparacyclophanes

Popis výsledku v původním jazyce

Simple switching of the site-selectivity of C-H activation reactions of substrates containing multiple directing groups is particularly important for the so-called late stage functionalization synthetic approach. In this work, we verified the possibility of achieving this by adding acids of different strengths. Using a substrate containing two differently strong (and basic) directing groups, the influence of the addition of acids on the regioselectivity of the C-H activation step of the reaction with palladium acetate was thoroughly studied. The addition of no or weak acids results in cyclopalladation being controlled by a stronger directing group. However, the addition of a strong acid causes protonation of this group and the reaction is then controlled by a weaker directing group. Finally, this approach enables double C-H activation leading to a unique class of compounds: &quot;non-symmetrical&quot; [2.2]-dipalladaparacyclophanes.

Název v anglickém jazyce

Switchable cyclopalladation of substrates containing two directing groups: on the way to non-symmetrical [2.2]-dipalladaparacyclophanes

Popis výsledku anglicky

Simple switching of the site-selectivity of C-H activation reactions of substrates containing multiple directing groups is particularly important for the so-called late stage functionalization synthetic approach. In this work, we verified the possibility of achieving this by adding acids of different strengths. Using a substrate containing two differently strong (and basic) directing groups, the influence of the addition of acids on the regioselectivity of the C-H activation step of the reaction with palladium acetate was thoroughly studied. The addition of no or weak acids results in cyclopalladation being controlled by a stronger directing group. However, the addition of a strong acid causes protonation of this group and the reaction is then controlled by a weaker directing group. Finally, this approach enables double C-H activation leading to a unique class of compounds: &quot;non-symmetrical&quot; [2.2]-dipalladaparacyclophanes.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach<br>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

Dalton Transactions

ISSN

1477-9226

e-ISSN

1477-9234

Svazek periodika

52

Číslo periodika v rámci svazku

32

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

7

Strana od-do

11113-11119

Kód UT WoS článku

001035920500001

EID výsledku v databázi Scopus

2-s2.0-85167334890