Microwave-Assisted Synthesis of Aryl β-Ketophosphonates via PdII Catalysis.
2024 (English)Independent thesis Advanced level (degree of Master (Two Years)), 30 credits / 45 HE credits
Student thesis
Abstract [en]
β-ketophosphonates are organophosphorus compounds of immense versatility. They resemble naturally occurring functionalities and have been utilized as enzyme inhibitors. Their reactivity is highlighted by their pivotal role in the Horner-Wadsworth-Emmons and Still-Gennari reactions to facilitate the stereoselective synthesis of alkenes. Consequently, the development of practical and efficient methodologies for β-ketophosphonate synthesis is of considerable importance. This study details the successful optimization of the PdII-catalyzed synthesis of aryl β-ketophosphonates via addition of aryl boronic acids to diethyl cyanomethyl phosphonate. The optimization processes involved a thorough evaluation of several parameters, including the catalyst system, solvent composition, temperature, reaction time, and atmospheric conditions. This accomplished the synthesis β-ketophosphonates with good yields in a relatively short timeframe. The method demonstrates high efficiency and practicality, providing a streamlined pathway for the synthesis of these invaluable compounds.
Place, publisher, year, edition, pages
2024.
Keywords [en]
optimization, palladium, catalysis, PdII, aryl boronic acids, phosphonate, nitrile, β-Ketophosphonates, PdII catalysis, cyanomethyl phosphonate, HWE, Horner-Wadsworth-Emmons, Still-Gennari
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-533568OAI: oai:DiVA.org:uu-533568DiVA, id: diva2:1878319
Educational program
Master Programme in Drug Discovery and Development
Supervisors
Examiners
2024-06-272024-06-262024-06-27Bibliographically approved