Preparation and transformations of acetophenone-derived enamino ketones, BF▫$_2$▫-▫$\beta$▫-ketoiminates, and BF▫$_2$▫-▫$\beta$▫-diketonates

Brodnik, Helena (author), Ciber, Luka (author), Grošelj, Uroš (author), Petek, Nejc (author), Štefane, Bogdan (author), Svete, Jurij (author)

A series of differently substituted β-enaminones 2a,b, 4a–i, 8a–d, and 9–13, their BF$_2$-β-ketoiminate complexes 5a–d, and BF$_2$-β-diketonate complexes 6a–d were prepared as model substrates for photochemical transformations. The attempted photochemical transformations of enaminones 2, 4, 8 and BF$_2$-β-ketoiminate complexes 5 failed. On the other hand, irradiation of mixtures of BF$_2$-β-diketonate complexes 6a–d and cycloalkanes with UV-A light (365 nm) gave the corresponding De Mayo reaction products 7a–f in 9–30% yields. The photochemical ring-expansion of acetyl tetralone-derived BF$_2$-complex 6d gave novel diannulated cyclooctane derivatives 7e and 7f, which would be difficult to obtain using conventional cyclization methods.

• Language: English
• Keywords: enaminones, ketoiminates, diketonates, transamination, photochemistry, De Mayo reaction, X-ray diffraction
• 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: 21 str.
• Numbering: Vol. 30, iss. 3, art. 601
• PID: 20.500.12556/RUL-167609
• UDC: 547.44.057
• ISSN on article: 1420-3049
• DOI: 10.3390/molecules30030601
• COBISS.SI-ID: 225004547
• Publication date in RUL: 04.03.2025

Record is a part of a journal

• Title: Molecules
• Shortened title: Molecules
• Publisher: MDPI
• ISSN: 1420-3049
• COBISS.SI-ID: 18462981

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: enaminoni, ketoiminati, diketonati, transaminiranje, fotokemija, De Mayo reakcija, rentgenska difrakcija

Projects

• Funder: ARIS - Slovenian Research and Innovation Agency
• Project number: P1-0179
• Name: Napredna organska sinteza in kataliza