Sequential catalytic carbonylation reactions for sustainable synthesis of biologically relevant entities

• Published in: Journal of organometallic chemistry 2020-09, Vol.923, p.121417, Article 121417
• Main Authors: Damas, Liliana, Rodrigues, Fábio M.S., Gonzalez, Andreia C.S., Carrilho, Rui M.B., Pineiro, Marta, Pereira, Mariette M.
• Format: Article
• Language: English
• Subjects: Aminocarbonylation; Chalcones; Hydroformylation; Microwave synthesis; N-heterocycles; Sequential reactions
• ISSN: 0022-328X; 1872-8561
• DOI: 10.1016/j.jorganchem.2020.121417

The sustainable synthesis of highly functionalised formylcarboxamide compounds with biological relevance is reported through a sequential aminocarbonylation/hydroformylation approach. The optimisation of palladium-catalysed aminocarbonylation of iodoaromatic substrates, using allylamine as nucleophile was first performed, with molybdenum hexacarbonyl as alternative CO source versus gaseous carbon monoxide. The combination of microwave irradiation with molybdenum hexacarbonyl allowed to selectively prepare a set of N-heterocyclic-based allylcarboxamides. Subsequent rhodium-catalysed hydroformylation of the allylcarboxamide intermediates led to the preparation of new pyridine, pyrazoline and chalcone derivatives containing both carboxamide and formyl moieties. [Display omitted] •Pd-catalysed aminocarbonylation of iodoaromatics using MW irradiation and Mo(CO)6 as CO source.•Synthesis of N-heterocyclic and chalcone-derived allylcarboxamides.•Catalytic aminocarbonylation/hydroformylation sequential process.•Synthesis of biologically relevant N-heterocyclic and chalcone derived formylcarboxamides.