Synthesis of 3-Carbonyl Trisubstituted Furans via Pd-Catalyzed Aerobic Cycloisomerization Reaction: Development and Mechanistic Studies

Autor(es)

Barboza, Amanda A. ^[1] ; Chiavegatti Neto, Attilio ^[1] ; Rosset, Isac G. ^{[1, 2]} ; Jardim, Guilherme A. M. ^[1] ; Ferreira, Marco A. B. ^[1]

Afiliação do(s) autor(es)

^[1] Fed Univ Sao Carlos UFSCar, Ctr Excellence Res Sustainable Chem CERSusChem, Dept Chem, BR-13565905 Sao Carlos, SP - Brazil

^[2] Univ Fed Parana, Dept Engn & Exatas, BR-85950000 Palotina, Parana - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of Organic Chemistry; v. 86, n. 5, p. 3923-3942, MAR 5 2021.
• Citações Web of Science: 0

Resumo

Herein, we report the synthesis of 3-carbonyltrisubstituted furans via Pd-catalyzed oxidative cycloisomerization reactions of 2-alkenyl-1,3-dicarbonyl scaffolds, using molecular oxygen as the sole oxidant to regenerate active palladium catalytic species, featuring good functional tolerance and mild reaction conditions. Deep investigation of intermediates and transition states of the reaction mechanism were conducted via experimental and DFT studies, providing a detailed mechanistical profile. The new developed methodology presents a greener alternative to Wacker-type cycloisomerizations and avoids the use of stoichiometric amounts of oxidants and strong acid additives. (AU)

• Processo FAPESP: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
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