Designing homogeneous copper-free Sonogashira reaction through a prism of Pd-Pd transmetalation

Martek, Bruno Aleksander (author), Gazvoda, Martin (author), Urankar, Damijana (author), Košmrlj, Janez (author)

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
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Year: 2020
• Number of pages: Str. 4938-4943
• Numbering: Vol. 22, iss. 13
• PID: 20.500.12556/RUL-125378
• UDC: 547:544.47:546.98
• ISSN on article: 1523-7060
• DOI: 10.1021/acs.orglett.0c01227
• COBISS.SI-ID: 14359811
• Publication date in RUL: 12.03.2021

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

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