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Designing homogeneous copper-free Sonogashira reaction through a prism of Pd-Pd transmetalation
ID Martek, Bruno Aleksander (Author), ID Gazvoda, Martin (Author), ID Urankar, Damijana (Author), ID Košmrlj, Janez (Author)

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Abstract
Simultaneous introduction of two different palladium (pre)catalysts, one tuned to promote oxidative addition to (hetero)aryl bromide and another to activate terminal alkyne substrate, leads to productive Pd−Pd transmetalation, subsequent reductive elimination, and formation of disubstituted alkyne. This conceptually novel rational design of copper-free Sonogashira reaction enabled facile identification of the reaction conditions, suitable for the synthesis of alkyl, aryl, and heteroaryl substituted alkynes at room temperature with as low as 0.125 mol % total Pd loading.

Language:English
Keywords:catalysis, palladium, Sonogashira reaction, alkyne, hydrocarbons, copper, ligands, addition reactions
Work type:Article (dk_c)
Typology:1.01 - Original Scientific Article
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2020
Publication status in journal:Published
Article version:Publisher's version of article
Number of pages:Str. 4938-4943
Numbering:Vol. 22, iss. 13
UDC:547:544.47:546.98
ISSN on article:1523-7060
DOI:10.1021/acs.orglett.0c01227 This link opens in a new window
COBISS.SI-ID:14359811 This link opens in a new window
Publication date in RUL:12.03.2021
Views:306
Downloads:140
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Record is a part of a journal

Title:Organic letters
Shortened title:Org. lett.
Publisher:American Chemical Society
ISSN:1523-7060
COBISS.SI-ID:1916442 This link opens in a new window

Licences

License:CC BY 4.0, Creative Commons Attribution 4.0 International
Link:http://creativecommons.org/licenses/by/4.0/
Description:This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.
Licensing start date:12.03.2021

Secondary language

Language:Slovenian
Keywords:kataliza, paladij, Sonogashira reakcija, alkini, hidrokarbonati, baker, ligandi, adicijske reakcije

Document is financed by a project

Funder:ARRS - Agencija za raziskovalno dejavnost Republike Slovenije (ARRS)
izpis_stevilka_projekta:P1-0230
Name:Organska kemija: sinteza, struktura in aplikacija

Funder:ARRS - Agencija za raziskovalno dejavnost Republike Slovenije (ARRS)
Funding Programme:Young Researcher Grant

Funder:ARRS - Agencija za raziskovalno dejavnost Republike Slovenije (ARRS)
izpis_stevilka_projekta:J1-8147
Name:Ligandi s tzNHC strukturo v organokovinski kemiji in homogeni katalizi: tvorba vezi C-C in C-N v vodi

Funder:ARRS - Agencija za raziskovalno dejavnost Republike Slovenije (ARRS)
izpis_stevilka_projekta:J1-9166
Name:Redefinicija in razširitev uporabe Sonogashirove reakcije pripajanja brez bakra

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