Palladium-Catalyzed Carbonylative Synthesis of Aryl Selenoesters Using Formic Acid as an Ex Situ CO Source

Author(s)

de Albuquerque, Danilo Yano ^[1] ; Teixeira, Wystan K. O. ^[1] ; do Sacramento, Manoela ^[2] ; Alves, Diego ^[2] ; Santi, Claudio ^[3] ; Schwab, Ricardo S. ^[1]

Affiliation

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

^[2] Univ Fed Pelotas UFPel, LASOL CCQFA, BR-96010900 Pelotas, RS - Brazil

^[3] Univ Perugia, Dept Pharmaceut Sci, Grp Catalysis Synth & Organ Green Chem, Via Liceo 1, I-06123 Perugia - Italy

• Document type: Journal article
• Source: Journal of Organic Chemistry; DEC 2021.
• Web of Science Citations: 0

Abstract

A new catalytic protocol for the synthesis of selenoesters from aryl iodides and diaryl diselenides has been developed, where formic acid was employed as an efficient, lowcost, and safe substitute for toxic and gaseous CO. This protocol presents a high functional group tolerance, providing access to a large family of selenoesters in high yields (up to 97%) while operating under mild reaction conditions, and avoids the use of selenol which is difficult to manipulate, easily oxidizes, and has a bad odor. Additionally, this method can be efficiently extended to the synthesis of thioesters with moderate-to-excellent yields, by employing for the first time diorganyl disulfides as precursors. (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: 13/06558-3 - Asymmetric catalysis: preparation of chiral alcohols and their derivatives from highly functionalized organozinc reagents and application of new chiral ligands supported on magnetic nanoparticles
• Grantee: Ricardo Samuel Schwab
• Support Opportunities: Regular Research Grants