Application of the Horner−Wadsworth−Emmons olefination in the construction of E‑α,β-unsaturated β‑boryl nitriles

Gosak, Kaja (author), Črnugelj, Martin (author), Časar, Zdenko (author)

Herein, we describe a simple transition-metal-free synthesis of E-α,β-unsaturated β-boryl nitriles by the Horner−Wadsworth−Emmons reaction starting from potassium acyltrifluoroborates. The methodology encompasses a broad range of alkyl and aryl substrates. The reaction conditions are simple, and the reaction products are in most cases isolated with good yields as pure E isomers without column chromatography.

• Language: English
• Keywords: olefination, boryl nitriles, differential scanning calorimetry, isolation, mixtures, stereoselectivity
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology; FFA - Faculty of Pharmacy
• Publication status: Published
• Publication version: Version of Record
• Year: 2025
• Number of pages: Str. 7498-7506
• Numbering: Vol. 90, iss. 22
• PID: 20.500.12556/RUL-176540
• UDC: 54
• ISSN on article: 0022-3263
• DOI: 10.1021/acs.joc.4c02915
• COBISS.SI-ID: 238524931
• Publication date in RUL: 03.12.2025

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.

Projects

• Funder: Sandoz company, Lek d.d.