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

Result code in 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>

Result on the web

<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>

Result language

angličtina

Original language name

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

Original language description

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.

Czech name

—

Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10403 - Physical chemistry

Project

—

Continuities

S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2023

Confidentiality

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

Name of the periodical

Dalton Transactions

ISSN

1477-9226

e-ISSN

1477-9234

Volume of the periodical

52

Issue of the periodical within the volume

32

Country of publishing house

GB - UNITED KINGDOM

Number of pages

7

Pages from-to

11113-11119

UT code for WoS article

001035920500001

EID of the result in the Scopus database

2-s2.0-85167334890