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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
Barboza, Amanda A. [1] ; Chiavegatti Neto, Attilio [1] ; Rosset, Isac G. [1, 2] ; Jardim, Guilherme A. M. [1] ; Ferreira, Marco A. B. [1]
Total Authors: 5
Affiliation:
[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
Total Affiliations: 2
Document type: Journal article
Source: Journal of Organic Chemistry; v. 86, n. 5, p. 3923-3942, MAR 5 2021.
Web of Science Citations: 0
Abstract

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)

FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
Grantee:Arlene Gonçalves Corrêa
Support Opportunities: Research Grants - Research Centers in Engineering Program
FAPESP's process: 20/10246-0 - Nuclear magnetic resonance spectroscopy: from pulse sequences to structural assignments
Grantee:Claudio Francisco Tormena
Support Opportunities: Research Projects - Thematic Grants
FAPESP's process: 20/01255-6 - Application of statistical tools in catalysis for understanding and predicting organic reactions
Grantee:Marco Antonio Barbosa Ferreira
Support Opportunities: Regular Research Grants