Ruthenium-catalyzed transfer hydrogenation of alkynes : access to alkanes and (E)- or (Z)‑alkenes in tandem with Pd/Cu Sonogashira cross-coupling

Jankovič, Dominik (author), Košmrlj, Janez (author), Gazvoda, Martin (author)

A complete reduction of alkynes using a combination of [RuCl$_2$(p-cymene)]$_2$, DTBM-SEGPHOS, and a paraformaldehyde/water system as the hydrogen source was developed, affording alkanes in 52–99% yields. In addition, the preparation of alkenes from terminal alkynes and aryl iodides by a tandem process of Pd/Cu-catalyzed Sonogashira reaction followed by Ru-catalyzed transfer hydrogenation is reported, affording alkenes in 38–99% yields. This multicatalysis proceeds via three consecutive reactions and can be extended further, as shown by adding an iodine-catalyzed cis–trans alkene isomerization step.

• Language: English
• Keywords: catalysts, ruthenium, chemical reactions, hydrocarbons, hydrogen, transfer 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: 2025
• Number of pages: Str. 3480-3484
• Numbering: Vol. 90, iss. 9
• PID: 20.500.12556/RUL-167895
• UDC: 547.31:66.094.25
• ISSN on article: 0022-3263
• DOI: 10.1021/acs.joc.4c01864
• COBISS.SI-ID: 229478915
• Publication date in RUL: 19.03.2025

Record is a part of a journal

• Title: Journal of organic chemistry
• Shortened title: J. org. chem.
• Publisher: American Chemical Society
• ISSN: 0022-3263
• COBISS.SI-ID: 235287

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.

Secondary language

• Language: Slovenian
• Keywords: katalizatorji, rutenij, kemijske reakcije, ogljikovodiki, vodik, reakcije prenosa